Back to results
US 5,958,496 AGranted
Aspartyl dipeptide amide derivatives and sweeteners
AssigneeAjinomoto Co., Inc.
InventorsYusuke Amino, Ryoichiro Nakamura, Tadashi Takemoto
Life of this patent
Estimating the term…
Abstract
Novel aspartyldipeptidoamides and salts thereof. The apartyldipeptides are useful as a low-calorie sweetener for food and beverage products and have excellent taste and chemical stability.
Claims28
An aspartyl dipeptide of formula (I):
- R.sub.1 --NHC.sup.1 H(CH.sub.2 COOH)CO--X--NH--C.sup.2 R.sub.2 R.sub.3 R.sub.4 (I)
- wherein
- R.sub.1 is a hydrogen atom or a hydrocarbon group having from 1 to 13 carbon atoms;
- R.sub.2 and R.sub.3 are each, independently, an alkyl group having from 1 to 3 carbon atoms, or
- C.sup.2, R.sub.2 and R.sub.3 together form a cycloalkyl group having from 3 to 6 carbon atoms, or
- R.sub.2 is a hydrogen atom and R.sub.3 is an alkylthioalkyl group having from 2 to 7 carbon atoms, an alkylsulfinylalkyl group having from 2 to 7 carbon atoms, an alkylsulfonylalkyl group having from 2 to 7 carbon atoms or an alkoxycarbonylmethyl group having from 2 to 7 carbon atoms;
- R.sub.4 is a phenyl group, a benzyl group, a cyclohexyl group, a cyclohexylmethyl group, a phenyl group substituted at the 2-, 3- or 4-position with a substituent selected from the group consisting of F, Cl, Br, I, a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, a cyano group, a nitro group, an acetyl group, an amino group and an acetylamino group, a phenyl group substituted at the position 2- and 3-positions or in the 3- and 4-positions with a substituent selected from the group consisting of a methylenedioxy group, a trimethylene group and a tetramethylene group, a 2-, 3- or 4-pyridyl group, a 2- or 3-furyl group, or a 2- or 3-thienyl group;
- X is an .alpha.-amino acid residue selected from the group consisting of D-alanine, D-.alpha.-aminobutyric acid, D-norvaline, D-valine, D-norleucine, D-leucine, D-isoleucine, D-alloisoleucine, D-t-leucine, D-serine, D-O-methylserine, D-threonine, D-O-methylthreonine, D-allothreonine, D-O-methylallothreonine, D-S-methylcysteine, D-methionine, D-phenylglycine, D-furylglycine and L-furylglycine, or X is a residue of a cyclic or acyclic .alpha., .alpha.-dialkylamino acid having from 3 to 6 carbon atoms;
- the configuration at the C.sup.1 -position is (S);
- the configuration at the C.sup.2 -position is (R) or (S) when at least two of R.sub.2, R.sub.3 and R.sub.4 are different,
- or a salt thereof.
8 more elements
A method of sweetening a food and/or a beverage comprising adding to a food and/or a beverage an effective amount of an aspartyl dipeptide of formula (I):
- R.sub.1 --NHC.sup.1 H(CH.sub.2 COOH)CO--X--NH--C.sup.2 R.sub.2 R.sub.3 R.sub.4 (I)
- wherein
- R.sub.1 is a hydrogen atom or a hydrocarbon group having from 1 to 13 carbon atoms;
- R.sub.2 and R.sub.3 are each, independently, an alkyl group having from 1 to 3 carbon atoms, or
- C.sup.2, R.sub.2 and R.sub.3 together form a cycloalkyl group having from 3 to 6 carbon atoms, or
- R.sub.2 is a hydrogen atom and R.sub.3 represents an alkylthioalkyl group having from 2 to 7 carbon atoms, an alkylsulfinylalkyl group having from 2 to 7 carbon atoms, an alkylsulfonylalkyl group having from 2 to 7 carbon atoms or an alkoxycarbonylmethyl group having from 2 to 7 carbon atoms;
- R.sub.4 is a phenyl group, a benzyl group, a cyclohexyl group, a cyclohexylmethyl group, a phenyl group substituted at the 2-, 3- or 4-position with a substituent selected from the group consisting of F, Cl, Br, I, a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, a cyano group, a nitro group, an acetyl group, an amino group and an acetylamino group, a phenyl group substituted at the position 2- and 3-positions or in the 3- and 4-positions with a substituent selected from the group consisting of a methylenedioxy group, a trimethylene group and a tetramethylene group, a 2-, 3- or 4-pyridyl group, a 2- or 3-furyl group, or a 2- or 3-thienyl group;
- X is an .alpha.-amino acid residue selected from the group consisting of D-alanine, D-.alpha.-aminobutyric acid, D-norvaline, D-valine, D-norleucine, D-leucine, D-isoleucine, D-alloisoleucine, D-t-leucine, D-serine, D-O-methylserine, D-threonine, D-O-methylthreonine, D-allothreonine, D-O-methylallothreonine, D-S-methylcysteine, D-methionine, D-phenylglycine, D-furylglycine and L-furylglycine, or X is a residue of a cyclic or acyclic .alpha., .alpha.-dialkylamino acid having from 3 to 6 carbon atoms;
- the configuration at the C.sup.1 -position is (S);
- the configuration at the C.sup.2 -position is (R) or (S) when at least two of R.sub.2, R.sub.3 and R.sub.4 are different,
- or a salt thereof.
8 more elements
Dependencies are inferred from the claim text.