Process for producing gamma-hydroxyamino acid derivatives and monatins
AssigneeAjinomoto Co., Inc.
InventorsYusuke Amino, Shigeru Kawahara
Life of this patent
Estimating the term…
Abstract
Dihydroisoxazole derivatives are conveniently converted to γ-hydroxyamino acid derivatives which are important as various synthetic intermediates by a catalytic hydrogenation reaction. High-purity monatins which may be used as sweeteners or ingredients thereof can be obtained by subjecting a 5-indolylmethyl-4,5-dihydroisoxazole-3,5-dicarboxylic acid to catalytic hydrogenation.
Claims22
A process for producing a γ-hydroxyamino acid derivative represented by the following formula (2) or a salt thereof:
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- said process comprising subjecting a dihydroisoxazole derivative represented by the following formula (1) or a salt thereof to catalytic hydrogenation
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- wherein
- R1 represents a hydrogen atom, a carboxyalkyl group having up to 20 carbon atoms, an alkyl group having up to 20 carbon atoms, an aryl group having up to 20 carbon atoms, an aralkyl group having up to 20 carbon atoms, or an heterocyclic ring(s)-containing hydrocarbon group having up to 20 carbon atoms;
- R2 and R3 each, independently of the other, represents a hydrogen atom, an alkyl group having up to 5 carbon atoms, or an aralkyl group having up to 12 carbon atoms;
- and
- each asymmetric carbon atom in formulae (1) and (2) may have a steric configuration of (R), (S) or (RS).
A process for preparing a sweetener composition, comprising:
- (1) catalytically reducing a dihydroisoxazole derivative represented by the following formula (1) or a salt thereof:
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- R1 represents a hydrogen atom, a carboxyalkyl group having up to 20 carbon atoms, an alkyl group having up to 20 carbon atoms, an aryl group having up to 20 carbon atoms, an aralkyl group having up to 20 carbon atoms, or an heterocyclic ring(s)-containing hydrocarbon group having up to 20 carbon atoms;
- and
- R2 and R3 each, independently of the other, represents a hydrogen atom, an alkyl group having up to 5 carbon atoms, or an aralkyl group having up to 12 carbon atoms,
- to obtain a γ-hydroxyamino acid derivative represented by the following formula (2) or a salt thereof:
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- wherein R1, R2, and R3 are as defined as above, and wherein each asymmetric carbon atom in formulae (1) and (2) may have a steric configuration of (R), (S) or (RS);
- and
- (2) mixing said γ-hydroxyamino acid derivative represented by formula (2) or a salt thereof with a food grade carrier or excipient or another sweetener.
Aprocess for preparing a sweetened food or beverage, comprising:
- (1) catalytically reducing a dihydroisoxazole derivative represented by the following formula (1) or a salt thereof:
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- R1 represents a hydrogen atom, a carboxyalkyl group having up to 20 carbon atoms, an alkyl group having up to 20 carbon atoms, an aryl group having up to 20 carbon atoms, an aralkyl group having up to 20 carbon atoms, or an heterocyclic ring(s)-containing hydrocarbon group having up to 20 carbon atoms;
- and
- R2 and R3 each, independently of the other, represents a hydrogen atom, an alkyl group having up to 5 carbon atoms, or an aralkyl group having up to 12 carbon atoms,
- to obtain a γ-hydroxyamino acid derivative represented by the following formula (2) or a salt thereof:
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- wherein R1, R2, and R3 are as defined as above, and wherein each asymmetric carbon atom in formulae (1) and (2) may have a steric configuration of (R), (S) or (RS);
- and
- (2) mixing said γ-hydroxyamino acid derivative represented by formula (2) or a salt thereof with a food or beverage.
Dependencies are inferred from the claim text.