Method for producing chain unsaturated carboxylic acid compound using phenylalanine ammonia layse
AssigneesRiken, Zeon Corporation, The Yokohama Rubber Co., Ltd.
InventorsTomokazu SHIRAI, Yutaro MORI, Yoshihide YACHI, Misao HIZA, Yayoi AKAHORI
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Abstract
A method for producing a chain-shaped unsaturated carboxylic acid compound or a geometric isomer thereof, having at least two carbon-carbon double bonds, including the steps of: removing, from a chain-shaped unsaturated carboxylic acid compound or a geometric isomer thereof having an amino group and a carbon-carbon double bond at a terminus, that amino group, in the presence of phenylalanine ammonia lyase, and further forming a carbon-carbon double bond.
Claims10
A method for producing a chain-shaped unsaturated carboxylic acid compound or a geometric isomer thereof, represented by the following formula (3), comprising the steps of:
- removing a first amino group from a chain-shaped unsaturated carboxylic acid compound or a geometric isomer thereof, having a first amino group and a first carbon-carbon double bond at a terminus, represented by the following formula (2), in the presence of phenylalanine ammonia lyase, and forming a second carbon-carbon double bond
- [in the formulas, (A) represents a linear hydrocarbon group having 0 to 5 carbon atoms, which may be substituted, and when the number of carbon atoms is 2 to 5, it may form a double bond between adjacent carbon atoms. R1 and R2 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a linear or branched alkoxy group having 1 to 5 carbon atoms, or a hydroxy group.].
A phenylalanine ammonia lyase variant into which at least one of the following amino acid substitutions (1) to (5) has been introduced:
- (1) position 108 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, is substituted with methionine, phenylalanine, or valine,
- (2) position 107 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, is substituted with tryptophan,
- (3) position 219 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, is substituted with isoleucine,
- (4) position 223 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, is substituted with isoleucine,
- (5) position 104 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, is substituted with alanine.
A method for producing a phenylalanine ammonia lyase variant, comprising the step of:
- introducing at least one of the following amino acid substitutions (1) to (5) into a phenylalanine ammonia lyase:
- (1) substituting position 108 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, with methionine, phenylalanine, or valine,
- (2) substituting position 107 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, with tryptophan,
- (3) substituting position 219 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, with isoleucine,
- (4) substituting position 223 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, with isoleucine,
- (5) substituting position 104 in the amino acid sequence set forth in SEQ ID NO:
- 2, or an amino acid corresponding to the position, with alanine.
Dependencies are inferred from the claim text.