CA2893950C - Preparation of poly alpha-1,3-glucan ethers - Google Patents

Preparation of poly alpha-1,3-glucan ethers Download PDF

Info

Publication number: CA2893950C
Authority: CA; Canada
Prior art keywords: glucan; poly alpha; reaction; alpha; preparation
Prior art date: 2012-12-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA2893950A

Other languages

English (en)

French (fr)

Other versions

CA2893950A1 (en

Inventor

Jayme L. Paullin

Andrea M. Perticone

Rahul B. Kasat

T. Joseph Dennes

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nutrition and Biosciences USA 4 Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2012-12-20

Filing date

2013-12-16

Publication date

2020-10-20

2013-12-16 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

2014-06-26 Publication of CA2893950A1 publication Critical patent/CA2893950A1/en

2020-10-20 Application granted granted Critical

2020-10-20 Publication of CA2893950C publication Critical patent/CA2893950C/en

Status Expired - Fee Related legal-status Critical Current

2033-12-16 Anticipated expiration legal-status Critical

Links

229920005640 poly alpha-1,3-glucan Polymers 0.000 title claims abstract description 361
150000002170 ethers Chemical class 0.000 title abstract description 74
238000002360 preparation method Methods 0.000 title description 71
238000006467 substitution reaction Methods 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 35
-1 ether compound Chemical class 0.000 claims description 126
238000006243 chemical reaction Methods 0.000 claims description 112
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 92
125000000962 organic group Chemical group 0.000 claims description 56
239000003795 chemical substances by application Substances 0.000 claims description 47
238000006266 etherification reaction Methods 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 21
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
125000004181 carboxyalkyl group Chemical group 0.000 claims description 17
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 79
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
239000007787 solid Substances 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
229920001503 Glucan Polymers 0.000 description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000002002 slurry Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 27
238000003756 stirring Methods 0.000 description 27
238000005481 NMR spectroscopy Methods 0.000 description 26
238000003828 vacuum filtration Methods 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
229910001854 alkali hydroxide Inorganic materials 0.000 description 21
150000008044 alkali metal hydroxides Chemical class 0.000 description 21
102000004190 Enzymes Human genes 0.000 description 19
108090000790 Enzymes Proteins 0.000 description 19
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 18
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 16
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 16
239000008103 glucose Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 16
238000001542 size-exclusion chromatography Methods 0.000 description 15
229920000642 polymer Polymers 0.000 description 14
239000011343 solid material Substances 0.000 description 14
108010055629 Glucosyltransferases Proteins 0.000 description 13
102000000340 Glucosyltransferases Human genes 0.000 description 13
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 13
229930006000 Sucrose Natural products 0.000 description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
239000011734 sodium Substances 0.000 description 13
229910052708 sodium Inorganic materials 0.000 description 13
239000005720 sucrose Substances 0.000 description 13
229930091371 Fructose Natural products 0.000 description 11
239000005715 Fructose Substances 0.000 description 11
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000000523 sample Substances 0.000 description 10
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
238000006911 enzymatic reaction Methods 0.000 description 9
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 9
238000002156 mixing Methods 0.000 description 9
WQZGKKKJIJFFOK-UHFFFAOYSA-N hexopyranose Chemical compound OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 8
229940050176 methyl chloride Drugs 0.000 description 8
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
125000004990 dihydroxyalkyl group Chemical group 0.000 description 7
238000012544 monitoring process Methods 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
230000003134 recirculating effect Effects 0.000 description 7
239000000126 substance Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
238000001816 cooling Methods 0.000 description 6
150000004676 glycans Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229920001282 polysaccharide Polymers 0.000 description 6
239000005017 polysaccharide Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
125000000547 substituted alkyl group Chemical group 0.000 description 6
239000000758 substrate Substances 0.000 description 6
DXALOGXSFLZLLN-WTZPKTTFSA-N (3s,4s,5r)-1,3,4,6-tetrahydroxy-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one Chemical compound OCC(=O)[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DXALOGXSFLZLLN-WTZPKTTFSA-N 0.000 description 5
JPFGFRMPGVDDGE-UHFFFAOYSA-N Leucrose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)(CO)OC1 JPFGFRMPGVDDGE-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
229960003750 ethyl chloride Drugs 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
230000008569 process Effects 0.000 description 5
239000012265 solid product Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
230000011987 methylation Effects 0.000 description 4
238000007069 methylation reaction Methods 0.000 description 4
229920001542 oligosaccharide Polymers 0.000 description 4
150000002482 oligosaccharides Chemical class 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 4
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 4
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 4
241000233866 Fungi Species 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
239000000835 fiber Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000005517 mercerization Methods 0.000 description 3
239000000178 monomer Substances 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
241000194024 Streptococcus salivarius Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000001348 alkyl chlorides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
229940089960 chloroacetate Drugs 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
150000002402 hexoses Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007523 nucleic acids Chemical class 0.000 description 2
108020004707 nucleic acids Proteins 0.000 description 2
102000039446 nucleic acids Human genes 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
229920000157 polyfructose Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003643 water by type Substances 0.000 description 2
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VNBFUGOVQMFIRN-UHFFFAOYSA-N 1-chlorobutan-2-ol Chemical compound CCC(O)CCl VNBFUGOVQMFIRN-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
AUNWZUQPAFGHFZ-UHFFFAOYSA-N 1-fluorosulfonyloxypropane Chemical compound CCCOS(F)(=O)=O AUNWZUQPAFGHFZ-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000045069 Agrocybe aegerita Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
240000008397 Ganoderma lucidum Species 0.000 description 1
235000001637 Ganoderma lucidum Nutrition 0.000 description 1
102000005744 Glycoside Hydrolases Human genes 0.000 description 1
108010031186 Glycoside Hydrolases Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
108010076504 Protein Sorting Signals Proteins 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-ZSJDYOACSA-N Sulfuric acid-d2 Chemical compound [2H]OS(=O)(=O)O[2H] QAOWNCQODCNURD-ZSJDYOACSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
108010048202 alternansucrase Proteins 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
SEXLAQXMAFCJCO-UHFFFAOYSA-N butyl trifluoromethanesulfonate Chemical compound CCCCOS(=O)(=O)C(F)(F)F SEXLAQXMAFCJCO-UHFFFAOYSA-N 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000013592 cell lysate Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
108010042194 dextransucrase Proteins 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
UVECLJDRPFNRRQ-UHFFFAOYSA-N ethyl trifluoromethanesulfonate Chemical compound CCOS(=O)(=O)C(F)(F)F UVECLJDRPFNRRQ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical group 0.000 description 1
KRRYGFCJUCTWMH-UHFFFAOYSA-N fluorosulfonyloxyethane Chemical compound CCOS(F)(=O)=O KRRYGFCJUCTWMH-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
108090001082 glucan-binding proteins Proteins 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000002608 ionic liquid Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000000569 multi-angle light scattering Methods 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008057 potassium phosphate buffer Substances 0.000 description 1
MJYCCJGURLWLGE-UHFFFAOYSA-N propyl trifluoromethanesulfonate Chemical compound CCCOS(=O)(=O)C(F)(F)F MJYCCJGURLWLGE-UHFFFAOYSA-N 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000004753 textile Substances 0.000 description 1
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

CA2893950A 2012-12-20 2013-12-16 Preparation of poly alpha-1,3-glucan ethers Expired - Fee Related CA2893950C (en)

Applications Claiming Priority (11)

Application Number	Priority Date	Filing Date	Title
US201261740106P	2012-12-20	2012-12-20
US201261740127P	2012-12-20	2012-12-20
US201261740076P	2012-12-20	2012-12-20
US201261740119P	2012-12-20	2012-12-20
US201261740087P	2012-12-20	2012-12-20
US61/740,119		2012-12-20
US61/740,076		2012-12-20
US61/740,106		2012-12-20
US61/740,087		2012-12-20
US61/740,127		2012-12-20
PCT/US2013/075285 WO2014099724A1 (en)	2012-12-20	2013-12-16	Preparation of poly alpha-1,3-glucan ethers

Publications (2)

Publication Number	Publication Date
CA2893950A1 CA2893950A1 (en)	2014-06-26
CA2893950C true CA2893950C (en)	2020-10-20

Family

ID=49917745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2893950A Expired - Fee Related CA2893950C (en)	2012-12-20	2013-12-16	Preparation of poly alpha-1,3-glucan ethers

Country Status (14)

Country	Link
EP (1)	EP2935339B1 (2)
JP (1)	JP6389470B2 (2)
KR (1)	KR20150096671A (2)
CN (1)	CN104854135B (2)
AU (1)	AU2013363174B2 (2)
CA (1)	CA2893950C (2)
CL (1)	CL2015001666A1 (2)
ES (1)	ES2740961T3 (2)
MX (1)	MX370288B (2)
MY (1)	MY168444A (2)
NZ (1)	NZ708491A (2)
PH (1)	PH12015501406B1 (2)
SG (1)	SG11201504397WA (2)
WO (1)	WO2014099724A1 (2)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT514137A1 (de)	2013-04-05	2014-10-15	Lenzing Akiengesellschaft	Polysaccharidfaser und Verfahren zu ihrer Herstellung
AT514468A1 (de)	2013-06-17	2015-01-15	Lenzing Akiengesellschaft	Hochsaugfähige Polysaccharidfaser und ihre Verwendung
AT514474B1 (de)	2013-06-18	2016-02-15	Chemiefaser Lenzing Ag	Polysaccharidfaser und Verfahren zu ihrer Herstellung
KR20160099629A (ko)	2013-12-16	2016-08-22	이 아이 듀폰 디 네모아 앤드 캄파니	점도 조절제로서의 폴리 알파-1,3-글루칸 에테르의 사용
ES2835703T3 (es)	2013-12-18	2021-06-23	Nutrition & Biosciences Usa 4 Inc	Eteres de poli alfa-1,3-glucano catiónicos
CN106103551A (zh)	2014-01-06	2016-11-09	纳幕尔杜邦公司	聚α‑1,3‑葡聚糖膜的制备
US10106626B2 (en)	2014-01-17	2018-10-23	Ei Du Pont De Nemours And Company	Production of poly alpha-1,3-glucan formate films
US9714403B2 (en)	2014-06-19	2017-07-25	E I Du Pont De Nemours And Company	Compositions containing one or more poly alpha-1,3-glucan ether compounds
EP3158043B1 (en)	2014-06-19	2021-03-10	Nutrition & Biosciences USA 4, Inc.	Compositions containing one or more poly alpha-1,3-glucan ether compounds
BR112017013368B1 (pt)	2014-12-22	2021-11-23	Nutrition & Biosciences USA 4, Inc.	Composição de mistura polimérica
US11351104B2 (en)	2015-02-06	2022-06-07	Nutrition & Biosciences USA 4, Inc.	Colloidal dispersions of poly alpha-1,3-glucan based polymers
AT518612B1 (de) *	2015-02-06	2019-03-15	Chemiefaser Lenzing Ag	Polysaccharid-Suspension, Verfahren zu ihrer Herstellung und ihre Verwendung
US10738266B2 (en)	2015-06-01	2020-08-11	Dupont Industrial Biosciences Usa, Llc	Structured liquid compositions comprising colloidal dispersions of poly alpha-1,3-glucan
CN107922512A (zh) *	2015-08-28	2018-04-17	纳幕尔杜邦公司	苄基α‑(1→3)‑葡聚糖及其纤维
CA2997563C (en)	2015-10-26	2022-03-22	E. I. Du Pont De Nemours And Company	Polysaccharide coatings for paper
ES2937288T3 (es)	2015-10-26	2023-03-27	Nutrition & Biosciences Usa 4 Inc	Composición de alfa-(1,3->glucano) insoluble en agua
EP3374401B1 (en)	2015-11-13	2022-04-06	Nutrition & Biosciences USA 4, Inc.	Glucan fiber compositions for use in laundry care and fabric care
JP7045313B2 (ja)	2015-11-13	2022-03-31	ニュートリション・アンド・バイオサイエンシーズ・ユーエスエー・フォー，インコーポレイテッド	洗濯ケアおよび織物ケアにおいて使用するためのグルカン繊維組成物
WO2017083226A1 (en)	2015-11-13	2017-05-18	E. I. Du Pont De Nemours And Company	Glucan fiber compositions for use in laundry care and fabric care
US10895028B2 (en)	2015-12-14	2021-01-19	Dupont Industrial Biosciences Usa, Llc	Nonwoven glucan webs
CN109312003A (zh) *	2016-06-13	2019-02-05	纳幕尔杜邦公司	洗涤剂组合物
US11028187B2 (en)	2016-06-13	2021-06-08	Nutrition & Biosciences USA 4, Inc.	Detergent compositions
BR112019009836B1 (pt) *	2016-11-16	2023-05-09	Nutrition & Biosciences Usa 4, Inc	Artigos, processo para a produção de um compósito e compósitos
JP2019536873A (ja) *	2016-11-22	2019-12-19	イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．ＤｕＰｏｎｔＤｅＮｅｍｏｕｒｓＡｎｄＣｏｍｐａｎｙ	ポリα−１，３−グルカンエステル及びこれより作製された物品
MX2019006868A (es) *	2016-12-16	2019-09-23	Du Pont	Derivados de polisacáridos anfifílicos y composiciones que los comprenden.
US11180889B2 (en) *	2017-01-24	2021-11-23	Nutrition & Biosciences USA 4, Inc.	Processes for producing precipitated calcium carbonate using polysaccharides
US11608417B2 (en) *	2017-06-30	2023-03-21	Nutrition & Biosciences USA 4, Inc.	Polysaccharide-elastomer masterbatch compositions
AU2018324496B2 (en) *	2017-09-01	2024-05-02	Nutrition & Biosciences USA 4, Inc.	Latex compositions comprising polysaccharides
WO2019075301A1 (en) *	2017-10-13	2019-04-18	E. I. Du Pont De Nemours And Company	Flowable bulk granular polysaccharide
WO2022235655A1 (en) *	2021-05-04	2022-11-10	Nutrition & Biosciences USA 4, Inc.	Compositions comprising insoluble alpha-glucan

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2000159806A (ja) *	1998-11-24	2000-06-13	Lion Corp	カルボキシメチル化ムタン並びに化粧料
CN1133654C (zh) *	1999-08-05	2004-01-07	武汉大学	灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法
CN1133653C (zh) *	1999-08-05	2004-01-07	武汉大学	灵芝α-(1→3)-D-葡聚糖硫酸酯衍生物及其用途和制备方法
JP4584146B2 (ja) *	2003-07-09	2010-11-17	江崎グリコ株式会社	α−１，４−グルカンおよび／またはその修飾物を含む成型物およびその製造方法

2013
- 2013-12-16 MY MYPI2015001373A patent/MY168444A/en unknown
- 2013-12-16 ES ES13817801T patent/ES2740961T3/es active Active
- 2013-12-16 WO PCT/US2013/075285 patent/WO2014099724A1/en not_active Ceased
- 2013-12-16 CN CN201380065899.9A patent/CN104854135B/zh active Active
- 2013-12-16 NZ NZ70849113A patent/NZ708491A/en not_active IP Right Cessation
- 2013-12-16 JP JP2015549524A patent/JP6389470B2/ja not_active Expired - Fee Related
- 2013-12-16 MX MX2015007768A patent/MX370288B/es active IP Right Grant
- 2013-12-16 EP EP13817801.7A patent/EP2935339B1/en active Active
- 2013-12-16 AU AU2013363174A patent/AU2013363174B2/en not_active Ceased
- 2013-12-16 CA CA2893950A patent/CA2893950C/en not_active Expired - Fee Related
- 2013-12-16 KR KR1020157016123A patent/KR20150096671A/ko not_active Abandoned
- 2013-12-16 SG SG11201504397WA patent/SG11201504397WA/en unknown
2015
- 2015-06-15 CL CL2015001666A patent/CL2015001666A1/es unknown
- 2015-06-18 PH PH12015501406A patent/PH12015501406B1/en unknown

Also Published As

Publication number	Publication date
KR20150096671A (ko)	2015-08-25
CL2015001666A1 (es)	2015-10-02
EP2935339A1 (en)	2015-10-28
PH12015501406A1 (en)	2015-09-14
MX370288B (es)	2019-12-09
EP2935339B1 (en)	2019-05-15
MX2015007768A (es)	2015-09-04
CN104854135A (zh)	2015-08-19
SG11201504397WA (en)	2015-07-30
PH12015501406B1 (en)	2015-09-14
CN104854135B (zh)	2018-06-22
JP6389470B2 (ja)	2018-09-12
JP2016503096A (ja)	2016-02-01
MY168444A (en)	2018-11-09
AU2013363174A1 (en)	2015-06-11
ES2740961T3 (es)	2020-02-07
WO2014099724A1 (en)	2014-06-26
NZ708491A (en)	2019-10-25
AU2013363174B2 (en)	2017-08-03
CA2893950A1 (en)	2014-06-26

Legal Events

Date	Code	Title	Description
2018-11-15	EEER	Examination request	Effective date: 20181113
2023-07-29	MKLA	Lapsed	Effective date: 20211216

Publication	Publication Date	Title
CA2893950C (en)	2020-10-20	Preparation of poly alpha-1,3-glucan ethers
US9139718B2 (en)	2015-09-22	Preparation of poly alpha-1,3-glucan ethers
Lin et al.	2019	An alkali-extracted polysaccharide from Zizyphus jujuba cv. Muzao: Structural characterizations and antioxidant activities
AU2016285548B2 (en)	2020-04-16	Preparation of poly alpha-1,3-glucan esters using cyclic organic anhydrides
Kim et al.	2000	Structural characterization of β-D-(1→ 3, 1→ 6)-linked glucans using NMR spectroscopy
JP6261610B2 (ja)	2018-01-17	ポリα−１，３−グルカンエステルの調製及びそれからのフィルム
Lin et al.	1994	Structure of chia seed polysaccharide exudate
JP6484252B2 (ja)	2019-03-13	ポリα−１，３−グルカンエステルの調製及びそれから製造されたフィルム
EP3161012A1 (en)	2017-05-03	Preparation of poly alpha-1,3-glucan ester films
Martin-Pastor et al.	2019	Structure, rheology, and copper-complexation of a hyaluronan-like exopolysaccharide from Vibrio
Zhang et al.	2020	Regioselective sulfation of β-glucan from Ganoderma lucidum and structure-anticoagulant activity relationship of sulfated derivatives
Glinel et al.	2000	Determination of substituents distribution in carboxymethylpullulans by NMR spectroscopy
Niu et al.	2016	Preparation and sulfation of an α-glucan from Actinidia chinensis roots and their potential activities
Matsuzaki et al.	1985	Synthesis of water‐soluble branched polysaccharides and their antitumor activity, 1. Branched polysaccharides from cellulose acetate
Vollmer et al.	2009	Comprehensive analysis of the substitution pattern in dextran ethers with respect to the reaction conditions
Rahelivao et al.	2014	Structure and rheological behaviour of agar extracted from Madagascar sea coast algae
Udoratina et al.	2012	Oxyethylated cellulose sulfates
JP2004099664A (ja)	2004-04-02	新規機能性材料としての硫酸化コンニャクマンナン及びその合成法。
Kardošová et al.	1997	A Fructofuranan from the Roots of Rudbeckia fulgida, var. sullivantii (BOYNTON et BEADLE)
Mahmood	1986	Studies on chemically modified xanthan
Tahir	2011	Alkynyl ethers of dextrans as Intermediates for new Functional Biopolymers