Method for producing optically active N-protected-propargylglycine
AssigneeSumitomo Chemical Company, Limited
InventorsYuki Takekawa, Isao Kurimoto
Life of this patent
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Abstract
A method for producing (S)-N-protected-propargylglycine of the following formula (2), wherein the method comprises asymmetrically hydrolyzing an N-protected-propargylglycine ester of the following formula (1) by using the following asymmetric hydrolysis enzyme or a cultured substance of a microorganism having an ability of producing this enzyme or a treated substance thereof. [Asymmetric Hydrolysis Enzyme] Hydrolysis enzymes derived from a microorganism selected from the group consisting of Thermomyces genus, Aspergillus genus, Rhizopus genus, Penicillium genus, Pseudomonas genus, Humicola genus, Burkholderia genus, Candida genus and Streptomyces genus.
Claims15
A method for producing (S)-N-protected-propargylglycine of the following formula (2), wherein the method comprises asymmetrically hydrolyzing an N-protected-propargylglycine ester of the following formula (1) by using the following asymmetric hydrolysis enzyme or a cultured substance of a microorganism having an ability of producing this enzyme or a treated substance thereof.
- (wherein, R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent a hydrogen atom or a protective group of an amino group, R2 and R3 being not simultaneously a hydrogen atom, and a carbon atom appended with a mark * represents an asymmetric carbon atom.).
- [Asymmetric hydrolysis enzyme]
- Hydrolysis enzymes derived from a microorganism selected from the group consisting of Thermomyces genus, Aspergillus genus, Rhizopus genus, Penicillium genus, Pseudomonas genus, Humicola genus, Burkholderia genus, Candida genus and Streptomyces genus.
A method for producing (R)-N-protected-propargylglycine wherein a (S)-N-protected-propargylglycine ester in an N-protected-propargylglycine ester of the following formula (1) is asymmetrically hydrolyzed by using the following asymmetric hydrolysis enzyme or a cultured substance of a microorganism having an ability of producing this enzyme or a treated substance thereof, then,
- (S)-N-protected-propargylglycine is separated, and an unreacted (R)-N-protected-propargylglycine ester is hydrolyzed.
- (wherein, R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent a hydrogen atom or a protective group of an amino group, R2 and R3 being not simultaneously a hydrogen atom, and a carbon atom appended with a mark * represents an asymmetric carbon atom.).
- [Asymmetric hydrolysis enzyme]
- Hydrolysis enzymes derived from a microorganism selected from the group consisting of Thermomyces genus, Aspergillus genus, Rhizopus genus, Penicillium genus, Pseudomonas genus, Humicola genus, Burkholderia genus, Candida genus and Streptomyces genus.
A method for producing
- (R)-N-protected-propargylglycine wherein a
- (S)-N-protected-propargylglycine ester in an
- N-protected-propargylglycine ester of the following formula (1) is asymmetrically hydrolyzed by using an esterase derived from a thermophilic microorganism.
- (wherein, R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent a hydrogen atom or a protective group of an amino group, R2 and R3 being not simultaneously a hydrogen atom, and a carbon atom appended with a mark * represents an asymmetric carbon atom)
Dependencies are inferred from the claim text.