EP0272564A2
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EP
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Enzyme mediated coupling reactions
Assignee: Hampshire Chemical Corp
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Filing: 1987-12-12
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Granted: —
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Expires: 2007-12-12
Abstract
Abstract Disclosed herein is an enzymatic process to bind two amino acids in the presence of a water-miscible solvent. Preferably the amino acids are precursors of aspartame and a preferred solvent is acetonitrile.
Inventors
- 👤 Akiva Tuvia Gross
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 12:22
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06104; C07K5/06113; C07K5/06121; C07K5/0613
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
65 words
In an enzymatic process to cause peptide bond formation between two substrates selected from the group consisting of N-substituted aspartic acid or a salt thereof and a phenylalanine lower alkyl ester wherein the benzylic carbon atom is substituted with hydrogen or one or more labile groups readily replaceable with hydrogen, the improvement comprising carrying out said process in the presence of a water-miscible organic solvent.
Claim 2
Dependent Claim
65 words
In an enzymatic process to cause peptide bond formation between two substrates selected from the group consisting of N-substituted aspartic acid or a salt thereof and a phenylalanine lower alkyl ester wherein the benzylic carbon atom is substituted with hydrogen or one or more labile groups readily replaceable with hydrogen, the improvement comprising carrying out said process in the presence of a water-miscible organic solvent.
Claim 3
Dependent Claim
20 words
A process as in Claim 1 wherein the reaction is carried out in the presence of a water-containing immobilized metalloproteinase.
Claim 4
Dependent Claim
11 words
A process as in Claim 1 wherein the enzyme is thermolysin.
Claim 5
Dependent Claim
14 words
A process as in Claim 1 wherein the N-protective group is formyl or benzyloxycarbonyl.
Claim 6
Dependent Claim
15 words
A process as in Claim 1 wherein the phenylalanine benzyl carbon is substituted with hydroxyl.
Claim 7
Dependent Claim
16 words
A process as in Claim 1 wherein the lower alkyl substituent of the ester is methyl.
Claim 8
Dependent Claim
11 words
A process as in Claim 1 wherein the solvent is acetonitrile.
Claim 9
Dependent Claim
19 words
A process as in Claim 1 wherein the process is carried out in the presence of an esterase inhibitor.
Claim 10
Dependent Claim
24 words
A process as in Claim 1 wherein the water-miscible solvent is a monohydric or polyhydric alcohol, a nitrile, an ether or a mixture thereof.
Claim 11
Dependent Claim
18 words
A process as in Claim 1 wherein the N-protective group is tertiary alkoxycarbonyl, benzyloxycarbonyl, p-toluenesulfonyl, o-nitrophenylsulfenyl, or formyl.
Claim 12
Dependent Claim
64 words
A process for manufacturing a dipeptide or polypeptide by reacting an acid component of an amino acid or peptide having an N-terminal protective group or a salt thereof with an amine component of an amino acid or peptide having a C-terminal protective group or a salt thereof in the presence of an enzyme known to mediate peptide bond formation and a solvent comprising acetonitrile.
Claim 13
Dependent Claim
64 words
A process for manufacturing a dipeptide or polypeptide by reacting an acid component of an amino acid or peptide having an N-terminal protective group or a salt thereof with an amine component of an amino acid or peptide having a C-terminal protective group or a salt thereof in the presence of an enzyme known to mediate peptide bond formation and a solvent comprising acetonitrile.
Claim 14
Dependent Claim
20 words
A process as in Claim 11 wherein the solvent is at least 50 wt.% acetonitrile and the balance is water.
Claim 15
Dependent Claim
29 words
A process as in Claim 11 wherein the solvent is at least 50 wt.% acetonitrile and the balance is water, one or more water-miscible organic solvents, or mixtures thereof.
Claim 16
Dependent Claim
11 words
A process as in Claim 11 wherein the enzyme is thermolysin.
Claim 17
Dependent Claim
18 words
A process as in Claim 11 wherein the amino acid having the N-terminal protective group is aspartic acid.
Claim 18
Dependent Claim
22 words
A process as in Claim 11 wherein the amino acid having the C-terminal protective group is a lower alkyl ester of phenylalanine.
Claim 19
Dependent Claim
17 words
A process as in Claim 16 wherein the protected amino acid is the methyl ester of phenylalanine.
Claim 20
Dependent Claim
14 words
A process as in Claim 15 wherein the N-protective group is formyl or benzyloxycarbonyl.
Claim 21
Dependent Claim
16 words
A process as in Claim 11 wherein an esterase inhibitor is present in the reaction mixture.
Claim 22
Dependent Claim
18 words
A process as in Claim 11 wherein the N-protective group is tertiary alkoxycarbonyl, benzyloxycarbonyl, p-toluenesulfonyl, o-nitrophenylsulfenyl, or formyl.
Claim 23
Dependent Claim
45 words
A process as in Claim 1 wherein the phenylalanine lower alkyl ester corresponds to the formula: wherein Ph is phenyl, X is -OH, -SH, -Cl, -Br, -I, -PCOCH₃, -OCOOCH₃, -NH₂ or SCH₃ and R is an alkyl group having from 1 to 4 carbon atoms.
Claim 24
Dependent Claim
14 words
A process as in Claim 21 wherein X is -OH and R is methyl.
Claim 25
Dependent Claim
17 words
A process as in Claim 11 wherein the amino acid having a C-terminal protective group is D-alanine.
References Cited (Backward Citations)
No citation records indexed.
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