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)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Nutrition Science (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 (uk)
EP (1)	EP1070726B1 (uk)
JP (1)	JP3959964B2 (uk)
KR (1)	KR100583547B1 (uk)
CN (1)	CN1181090C (uk)
AR (1)	AR018592A1 (uk)
AT (1)	ATE386445T1 (uk)
AU (1)	AU753110B2 (uk)
BR (1)	BR9909542B1 (uk)
CA (1)	CA2327938C (uk)
CZ (1)	CZ299112B6 (uk)
DE (1)	DE69938177T2 (uk)
ES (1)	ES2299252T3 (uk)
HU (1)	HU228909B1 (uk)
IL (2)	IL138619A0 (uk)
NO (1)	NO325350B1 (uk)
NZ (1)	NZ507938A (uk)
OA (1)	OA11537A (uk)
PL (1)	PL197801B1 (uk)
RU (1)	RU2179979C1 (uk)
SK (1)	SK286552B6 (uk)
TR (1)	TR200002929T2 (uk)
TW (1)	TW530066B (uk)
UA (1)	UA63007C2 (uk)
WO (1)	WO1999052937A1 (uk)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100583547B1 (ko)	1998-04-09	2006-05-26	아지노모토 가부시키가이샤	아스파르틸 디펩타이드 에스테르 유도체, 이를 포함하는 감미제 및 당해 감미제를 포함하는 식품
IL139657A0 (en) *	1998-06-26	2002-02-10	Ajinomoto Kk	Novel aspartyl dipeptide ester derivatives and sweeteners
SK3682001A3 (en) *	1998-09-18	2001-10-08	Ajinomoto Kk	N-alkylaspartyldipeptide ester derivatives and sweeteners
WO2001018034A1 (en) *	1999-09-07	2001-03-15	Ajinomoto Co., Inc.	Process for producing aspartame derivative, method of purifying the same, crystals thereof and use of the same
JP2001097998A (ja) *	1999-10-01	2001-04-10	Ajinomoto Co Inc	アスパルチルジペプチドエステル誘導体及び甘味剤
AU7321900A (en) *	1999-10-07	2001-05-10	Ajinomoto Co., Inc.	Process for the production of aspartyldipeptide ester derivatives, novel intermediates therefor and process for the production of the intermediates
WO2001025259A1 (en) *	1999-10-07	2001-04-12	Ajinomoto Co., Inc.	Processes for producing and purifying aspartame derivatives and process for producing production intermediates
WO2001027142A1 (en) *	1999-10-08	2001-04-19	Ajinomoto Co., Inc.	Process for producing aspartame derivative, crystals thereof, novel production intermediates therefor and process for producing the intermediate
CN1391553A (zh)	1999-11-18	2003-01-15	味之素株式会社	高甜度甜味剂用的新型中间体以及它的制造方法
RU2222544C1 (ru) *	1999-12-28	2004-01-27	Адзиномото Ко., Инк.	Кристалл производного аспартама
JP2001199930A (ja)	2000-01-20	2001-07-24	Ajinomoto Co Inc	新規アリ−ルプロピルアルデヒド誘導体、その製造法及びその使用等
JP3747737B2 (ja) *	2000-05-10	2006-02-22	日本電気株式会社	広域精細画像生成方法及びシステム並びにコンピュータ可読記録媒体
CN1429234A (zh) *	2000-05-10	2003-07-09	味之素株式会社	天冬氨酰基二肽酯衍生物的制备方法
KR100776924B1 (ko)	2000-05-16	2007-11-20	아지노모토 가부시키가이샤	신나밀알데히드 유도체의 제조방법 및 이의 사용
CA2437655A1 (en) *	2001-02-08	2002-08-15	Ajinomoto Co., Inc.	Novel n-alkylaspartyl amide derivative and sweetening agent
KR20110060969A (ko) *	2003-05-06	2011-06-08	뉴트라스위트 프라퍼티 홀딩스 인코포레이티드	3,3-디메틸부티르알데히드 전구체를 이용한 Ｎ-(Ｎ-(3,3-디메틸부틸)-Ｌ-α-아스파르틸)-Ｌ-페닐알라닌 1-메틸 에스테르의 합성
NZ580640A (en) *	2007-05-08	2012-02-24	Ajinomoto Kk	Sweetner comprising a compound having a calcium receptor-activating effect
CN102206245A (zh) *	2011-01-17	2011-10-05	汪志强	一种甜味剂艾克·本甜的制备方法及其在饲料领域的用途
JP6498455B2 (ja) *	2014-02-03	2019-04-10	三栄源エフ・エフ・アイ株式会社	高甘味度甘味料の味質改善剤及び味質改善方法
WO2016009686A1 (ja) *	2014-07-16	2016-01-21	味の素株式会社	風味の向上した食肉及び食肉加工品並びにその製造方法
IN2015CH02019A (uk)	2015-04-20	2015-06-05	Divis Lab Ltd
JP5964528B1 (ja) *	2016-03-08	2016-08-03	長谷川香料株式会社	４−アルコキシシンナムアルデヒドを有効成分とする香味変調剤
CN119954888B (zh) *	2025-01-17	2026-03-17	深圳市华加生物科技有限公司	一种新型二肽类甜味剂及其合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2533210A1 (fr) *	1982-09-17	1984-03-23	Lyon I Universite Claude	Edulcorants de synthese
FR2653303B1 (fr) *	1989-10-24	1992-09-18	Noffre Claude	Agents edulcorants de grande stabilite derivant des acides l-aspartique et l-glutamique n-hydrocarbones 1-oxo-2-ramifies.
FR2697844B1 (fr) *	1992-11-12	1995-01-27	Claude Nofre	Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation.
JP2777329B2 (ja)	1994-03-24	1998-07-16	日本碍子株式会社	粘弾性測定方法
FR2729950B1 (fr) *	1995-01-26	1997-04-18	Univ Claude Bernard Lyon	Nouveaux agents edulcorants derivant des acides n-(4- cyanophenylcarbamoyl ou 2-cyanopyrid-5-ylcarbamoyl)-l- aspartique ou l-glutamique alpha-benzenamides
JPH10259194A (ja)	1997-03-18	1998-09-29	Ajinomoto Co Inc	新規ジペプチド誘導体及び甘味剤
KR100583547B1 (ko)	1998-04-09	2006-05-26	아지노모토 가부시키가이샤	아스파르틸 디펩타이드 에스테르 유도체, 이를 포함하는 감미제 및 당해 감미제를 포함하는 식품

1999
- 1999-03-11 KR KR1020007011145A patent/KR100583547B1/ko not_active Expired - Lifetime
- 1999-03-11 OA OA1200000278A patent/OA11537A/en unknown
- 1999-03-11 RU RU2000128012/04A patent/RU2179979C1/ru active
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- 1999-03-11 NZ NZ507938A patent/NZ507938A/xx not_active IP Right Cessation
- 1999-03-11 TR TR2000/02929T patent/TR200002929T2/xx unknown
- 1999-03-11 WO PCT/JP1999/001210 patent/WO1999052937A1/ja not_active Ceased
- 1999-03-11 PL PL343377A patent/PL197801B1/pl unknown
- 1999-03-11 ES ES99932431T patent/ES2299252T3/es not_active Expired - Lifetime
- 1999-03-11 DE DE69938177T patent/DE69938177T2/de not_active Expired - Lifetime
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- 1999-03-11 IL IL13861999A patent/IL138619A0/xx active IP Right Grant
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Also Published As

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

Publication	Publication Date	Title
JP3959964B2 (ja)	2007-08-15	アスパルチルジペプチドエステル誘導体及び甘味剤
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
US5795612A (en)	1998-08-18	Aspartyldipeptideamine derivatives and sweetner
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