OA11537A - Aspartyl dipeptide ester derivatives and sweeteners. - Google Patents

Aspartyl dipeptide ester derivatives and sweeteners. Download PDF

Info

Publication number: OA11537A
Authority: OA; OAPI
Prior art keywords: group; dérivatives; methyl; hydrogen atoms; aspartyl
Prior art date: 1998-04-09

Application number

OA1200000278A

Other languages

English (en)

Inventor

Yusuke Amino

Kazuko Yuzawa

Tadashi Takemoto

Ryoichiro Nakamura

Original Assignee

Ajinomoto Kk

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.)

1998-04-09

Filing date

1999-03-11

Publication date

2004-05-24

1999-03-11 Application filed by Ajinomoto Kk filed Critical Ajinomoto Kk

2004-05-24 Publication of OA11537A publication Critical patent/OA11537A/en

Links

-1 Aspartyl Chemical group 0.000 title claims abstract description 52
235000003599 food sweetener Nutrition 0.000 title claims abstract description 23
239000003765 sweetening agent Substances 0.000 title claims abstract description 23
150000002148 esters Chemical class 0.000 title claims abstract description 13
108010016626 Dipeptides Proteins 0.000 title claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
235000013305 food Nutrition 0.000 claims description 4
239000004067 bulking agent Substances 0.000 claims description 2
101100001686 Burkholderia cepacia andR gene Proteins 0.000 claims 1
235000010357 aspartame Nutrition 0.000 abstract description 60
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 abstract description 57
230000000694 effects Effects 0.000 abstract description 2
229960005190 phenylalanine Drugs 0.000 description 53
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 52
150000001875 compounds Chemical class 0.000 description 33
230000015572 biosynthetic process Effects 0.000 description 23
238000003786 synthesis reaction Methods 0.000 description 23
239000007787 solid Substances 0.000 description 22
CQLWFQJPXFAGOR-UHFFFAOYSA-N 3-(4-methoxy-3-phenylmethoxyphenyl)prop-2-enal Chemical compound COC1=CC=C(C=CC=O)C=C1OCC1=CC=CC=C1 CQLWFQJPXFAGOR-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
230000002829 reductive effect Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
108010011485 Aspartame Proteins 0.000 description 6
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical group OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 6
239000000605 aspartame Substances 0.000 description 6
229960003438 aspartame Drugs 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000000034 method Methods 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KJPRLNWUNMBNBZ-UHFFFAOYSA-N 3-phenylprop-2-enal Chemical compound O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 4
AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000012046 mixed solvent Substances 0.000 description 4
125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
KPNHONAEPLEAJL-UHFFFAOYSA-N 2-methoxy-3-phenylprop-2-enal Chemical compound COC(C=O)=CC1=CC=CC=C1 KPNHONAEPLEAJL-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229960004441 tyrosine Drugs 0.000 description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
235000003704 aspartic acid Nutrition 0.000 description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
HLIAVLHNDJUHFG-UHFFFAOYSA-N neotame Chemical compound CC(C)(C)CCNC(CC(O)=O)C(=O)NC(C(=O)OC)CC1=CC=CC=C1 HLIAVLHNDJUHFG-UHFFFAOYSA-N 0.000 description 2
KKVZAVRSVHUSPL-UHFFFAOYSA-N o-methoxycinnamic aldehyde Natural products COC1=CC=CC=C1C=CC=O KKVZAVRSVHUSPL-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000005932 reductive alkylation reaction Methods 0.000 description 2
230000001953 sensory effect Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
NIXBWPAGYLGLIW-ONEGZZNKSA-N (e)-3-(2,4-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=C(\C=C\C=O)C(OC)=C1 NIXBWPAGYLGLIW-ONEGZZNKSA-N 0.000 description 1
XHYAQFCRAQUBTD-HWKANZROSA-N (e)-3-(3-methoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(\C=C\C=O)=C1 XHYAQFCRAQUBTD-HWKANZROSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VLUMOWNVWOXZAU-UHFFFAOYSA-N 2-methyl-3-phenylprop-2-enal Chemical compound O=CC(C)=CC1=CC=CC=C1 VLUMOWNVWOXZAU-UHFFFAOYSA-N 0.000 description 1
KNUFNLWDGZQKKJ-ONEGZZNKSA-N 3,4-dimethoxy cinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1OC KNUFNLWDGZQKKJ-ONEGZZNKSA-N 0.000 description 1
MAEJAIDDJLODOP-UHFFFAOYSA-N 3-(2-ethoxy-4-methoxyphenyl)prop-2-enal Chemical compound CCOC1=CC(OC)=CC=C1C=CC=O MAEJAIDDJLODOP-UHFFFAOYSA-N 0.000 description 1
CINMFLQINIXMBH-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC(OC)=CC(C=CC=O)=C1 CINMFLQINIXMBH-UHFFFAOYSA-N 0.000 description 1
HGTOAFUUSJILGJ-UHFFFAOYSA-N 3-(3-methoxy-2-phenylmethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OCC1=CC=CC=C1 HGTOAFUUSJILGJ-UHFFFAOYSA-N 0.000 description 1
NRHHRVCIHKGMAJ-UHFFFAOYSA-N 3-(3-methyl-4-phenylmethoxyphenyl)prop-2-enal Chemical compound CC1=CC(C=CC=O)=CC=C1OCC1=CC=CC=C1 NRHHRVCIHKGMAJ-UHFFFAOYSA-N 0.000 description 1
QBEWPLRZBMVYKF-UHFFFAOYSA-N 3-(4-ethoxyphenyl)prop-2-enal Chemical compound CCOC1=CC=C(C=CC=O)C=C1 QBEWPLRZBMVYKF-UHFFFAOYSA-N 0.000 description 1
TWDQLRXKJLPFBR-UHFFFAOYSA-N 3-(4-methoxy-2-phenylmethoxyphenyl)prop-2-enal Chemical compound COC1=CC=C(C=CC=O)C(OCC=2C=CC=CC=2)=C1 TWDQLRXKJLPFBR-UHFFFAOYSA-N 0.000 description 1
IJNZQGWGATTXNO-UHFFFAOYSA-N 3-(4-methoxy-3-methylphenyl)prop-2-enal Chemical compound COC1=CC=C(C=CC=O)C=C1C IJNZQGWGATTXNO-UHFFFAOYSA-N 0.000 description 1
HRWFESZBHWFBRA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-phenylmethoxyprop-2-enal Chemical compound C(C1=CC=CC=C1)OC(C=O)=CC1=CC=C(C=C1)OC HRWFESZBHWFBRA-UHFFFAOYSA-N 0.000 description 1
YXYBWGVCPPIKHN-UHFFFAOYSA-N 3-(4-methyl-2-phenylmethoxyphenyl)prop-2-enal Chemical compound CC1=CC=C(C=CC=O)C(OCC=2C=CC=CC=2)=C1 YXYBWGVCPPIKHN-UHFFFAOYSA-N 0.000 description 1
ADWYCCMFSHPNOT-UHFFFAOYSA-N 3-(4-methyl-3-phenylmethoxyphenyl)prop-2-enal Chemical compound CC1=CC=C(C=CC=O)C=C1OCC1=CC=CC=C1 ADWYCCMFSHPNOT-UHFFFAOYSA-N 0.000 description 1
NYHQCCMTIODLDK-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)prop-2-enal Chemical compound C1=CC(C=CC=O)=CC=C1OCC1=CC=CC=C1 NYHQCCMTIODLDK-UHFFFAOYSA-N 0.000 description 1
PQDBOHWVSPBQMR-UHFFFAOYSA-N 3-[4-(2-hydroxyethoxy)phenyl]prop-2-enal Chemical compound OCCOC1=CC=C(C=CC=O)C=C1 PQDBOHWVSPBQMR-UHFFFAOYSA-N 0.000 description 1
LVWQDUNNVPYRQC-UHFFFAOYSA-N 3-phenyl-2-phenylmethoxyprop-2-enal Chemical compound C=1C=CC=CC=1C=C(C=O)OCC1=CC=CC=C1 LVWQDUNNVPYRQC-UHFFFAOYSA-N 0.000 description 1
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical class O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XHAGTHLWALCIKI-UHFFFAOYSA-N 5-phenyl-1,3-dioxole-4-carbaldehyde Chemical compound O1COC(C=O)=C1C1=CC=CC=C1 XHAGTHLWALCIKI-UHFFFAOYSA-N 0.000 description 1
KNUFNLWDGZQKKJ-UHFFFAOYSA-N Anticancer Benzenoid PMV70P691-57 Natural products COC1=CC=C(C=CC=O)C=C1OC KNUFNLWDGZQKKJ-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241000404146 Minois Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
108010041382 compound 20 Proteins 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
235000006694 eating habits Nutrition 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
RBAUAHIPDXKQJI-QMMMGPOBSA-N methyl (2s)-2-anilinopropanoate Chemical compound COC(=O)[C@H](C)NC1=CC=CC=C1 RBAUAHIPDXKQJI-QMMMGPOBSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Nutrition Science (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Peptides Or Proteins (AREA)
Seasonings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

OA1200000278A 1998-04-09 1999-03-11 Aspartyl dipeptide ester derivatives and sweeteners. OA11537A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9770198		1998-04-09
JP3819099		1999-02-17

Publications (1)

Publication Number	Publication Date
OA11537A true OA11537A (en)	2004-05-24

Family

ID=26377391

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000278A OA11537A (en)	1998-04-09	1999-03-11	Aspartyl dipeptide ester derivatives and sweeteners.

Country Status (25)

Country	Link
US (1)	US6548096B1 (pl)
EP (1)	EP1070726B1 (pl)
JP (1)	JP3959964B2 (pl)
KR (1)	KR100583547B1 (pl)
CN (1)	CN1181090C (pl)
AR (1)	AR018592A1 (pl)
AT (1)	ATE386445T1 (pl)
AU (1)	AU753110B2 (pl)
BR (1)	BR9909542B1 (pl)
CA (1)	CA2327938C (pl)
CZ (1)	CZ299112B6 (pl)
DE (1)	DE69938177T2 (pl)
ES (1)	ES2299252T3 (pl)
HU (1)	HU228909B1 (pl)
IL (2)	IL138619A0 (pl)
NO (1)	NO325350B1 (pl)
NZ (1)	NZ507938A (pl)
OA (1)	OA11537A (pl)
PL (1)	PL197801B1 (pl)
RU (1)	RU2179979C1 (pl)
SK (1)	SK286552B6 (pl)
TR (1)	TR200002929T2 (pl)
TW (1)	TW530066B (pl)
UA (1)	UA63007C2 (pl)
WO (1)	WO1999052937A1 (pl)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1999
- 1999-03-11 RU RU2000128012/04A patent/RU2179979C1/ru active
- 1999-03-11 OA OA1200000278A patent/OA11537A/en unknown
- 1999-03-11 AU AU41184/99A patent/AU753110B2/en not_active Expired
- 1999-03-11 CN CNB998049204A patent/CN1181090C/zh not_active Expired - Lifetime
- 1999-03-11 TR TR2000/02929T patent/TR200002929T2/xx unknown
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- 1999-03-11 JP JP2000543493A patent/JP3959964B2/ja not_active Expired - Lifetime
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- 1999-03-11 DE DE69938177T patent/DE69938177T2/de not_active Expired - Lifetime
- 1999-03-11 WO PCT/JP1999/001210 patent/WO1999052937A1/ja not_active Ceased
- 1999-03-11 CZ CZ20003730A patent/CZ299112B6/cs not_active IP Right Cessation
- 1999-03-11 AT AT99932431T patent/ATE386445T1/de active
- 1999-03-11 HU HU0101682A patent/HU228909B1/hu unknown
- 1999-03-11 IL IL13861999A patent/IL138619A0/xx active IP Right Grant
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- 1999-03-11 PL PL343377A patent/PL197801B1/pl unknown
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- 1999-03-11 BR BRPI9909542-4A patent/BR9909542B1/pt not_active IP Right Cessation
- 1999-03-11 KR KR1020007011145A patent/KR100583547B1/ko not_active Expired - Lifetime
- 1999-03-17 TW TW088104155A patent/TW530066B/zh not_active IP Right Cessation
- 1999-04-07 AR ARP990101566A patent/AR018592A1/es active IP Right Grant
- 1999-11-03 UA UA2000116315A patent/UA63007C2/uk unknown
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Also Published As

Publication number	Publication date
DE69938177D1 (de)	2008-04-03
DE69938177T2 (de)	2008-11-06
KR100583547B1 (ko)	2006-05-26
NO20004979D0 (no)	2000-10-03
ATE386445T1 (de)	2008-03-15
IL138619A0 (en)	2001-10-31
PL343377A1 (en)	2001-08-13
EP1070726B1 (en)	2008-02-20
CA2327938A1 (en)	1999-10-21
CZ299112B6 (cs)	2008-04-23
EP1070726A4 (en)	2005-01-19
BR9909542B1 (pt)	2011-04-19
TW530066B (en)	2003-05-01
US6548096B1 (en)	2003-04-15
PL197801B1 (pl)	2008-04-30
CN1181090C (zh)	2004-12-22
CZ20003730A3 (cs)	2001-04-11
RU2179979C1 (ru)	2002-02-27
NO20004979L (no)	2000-11-07
AU753110B2 (en)	2002-10-10
ES2299252T3 (es)	2008-05-16
CA2327938C (en)	2010-12-07
IL138619A (en)	2007-03-08
HU228909B1 (en)	2013-06-28
JP3959964B2 (ja)	2007-08-15
HUP0101682A2 (hu)	2001-12-28
AR018592A1 (es)	2001-11-28
RU2000128012A (ru)	2004-03-20
BR9909542A (pt)	2000-12-26
CN1296493A (zh)	2001-05-23
WO1999052937A1 (en)	1999-10-21
HUP0101682A3 (en)	2003-04-28
SK15042000A3 (sk)	2001-04-09
UA63007C2 (uk)	2004-01-15
EP1070726A1 (en)	2001-01-24
NO325350B1 (no)	2008-04-07
KR20010042515A (ko)	2001-05-25
SK286552B6 (sk)	2008-12-05
AU4118499A (en)	1999-11-01
TR200002929T2 (tr)	2001-03-21
NZ507938A (en)	2002-11-26

Publication	Publication Date	Title
OA11537A (en)	2004-05-24	Aspartyl dipeptide ester derivatives and sweeteners.
JPWO1999052937A1 (ja)	2002-10-29	アスパルチルジペプチドエステル誘導体及び甘味剤
RU2192430C2 (ru)	2002-11-10	Новые производные аспартилового дипептидного эфира и подсластители
AU748136B2 (en)	2002-05-30	N-alkylaspartyldipeptide ester derivatives and sweeteners
CA2165721A1 (en)	1996-12-13	Novel aspartyldipeptide amide derivatives and sweetener
MXPA00009449A (es)	2001-07-09	Edulcorantes y derivados de ester dipeptido aspartilo
US6649784B2 (en)	2003-11-18	Aspartyl dipeptide ester derivatives and sweeteners
JP2002234898A (ja)	2002-08-23	新規ｎ−アルキルアスパルチルジペプチド誘導体及び甘味剤
MXPA00012122A (es)	2002-06-05	Derivados y edulcorantes de ester dipeptido de aspartilo novedosos
MXPA01002402A (en)	2003-02-17	N-alkylaspartyldipeptide ester derivatives and sweeteners
CZ20004873A3 (cs)	2001-06-13	Esterové deriváty aspartyldipeptidu
JP2001322996A (ja)	2001-11-20	新規ｎ−アルキルアスパルチルジペプチドエステル誘導体及び甘味剤
JPWO2000017230A1 (ja)	2001-12-11	Ｎ−アルキルアスパルチルジペプチドエステル誘導体及び甘味剤