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US 11,396,666 B2Granted
Method for producing (1R,3R)-3-(trifluoromethyl)cyclohexan-1-ol and intermediate thereof
AssigneeApi Corporation
InventorsHaruka Sasano, Takanobu Iura, Kenji Oki
Life of this patent
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Abstract
A method for producing a compound represented by formula (3) including bringing a carbon-carbon double bond reductase, a microorganism or cell having an ability to produce the enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the enzyme which is obtained by culturing the microorganism or cell, and a carbonyl reductase, a microorganism or cell having an ability to produce the enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the enzyme which is obtained by culturing the microorganism or cell into contact with a compound represented by formula (1) to obtain a compound represented by formula (3):
Claims8
A method for producing a compound represented by the formula (3):
- comprising:
- bringing a carbon-carbon double bond reductase enzyme, a microorganism or cell having an ability to produce the carbon-carbon double bond reductase enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the carbon-carbon double bond reductase enzyme which is obtained by culturing the microorganism or cell, and a carbonyl reductase enzyme, a microorganism or cell having an ability to produce the carbonyl reductase enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the carbonyl reductase enzyme which is obtained by culturing the microorganism or cell into contact with a compound represented by the formula (1):
- to obtain the compound represented by the formula (3);
- wherein:
- the carbon-carbon double bond reductase enzyme comprises a protein shown in the following (A), (B), or (C):
- (A) a protein having the amino acid sequence shown in SEQ ID NO:
- 1;
- (B) a protein having an amino acid sequence resulting from deletion, substitution, insertion, and/or addition of 1 to 50 amino acids in the amino acid sequence shown in SEQ ID NO:
- 1, and having an activity to catalyze reaction(s) shown in the formula (I) and/or the formula (II):
- (C) a protein having an amino acid sequence with not less than 85% identity with the amino acid sequence shown in SEQ ID NO:
- 1, having at least one amino acid substitution selected from the following groups (i) and (ii) introduced thereinto, and having an activity to catalyze reaction(s) shown in the formula (I) and/or the formula (II):
- (i) substitution of the 26th cysteine in the amino acid sequence shown in SEQ ID NO:
- 1 with an amino acid other than aspartic acid, phenylalanine, tryptophan, and tyrosine,
- (ii) substitution of the 104th alanine in the amino acid sequence shown in SEQ ID NO:
- 1 with an amino acid other than alanine;
- and
- the carbonyl reductase enzyme comprises a protein shown in the following (D), (E), or (F):
- (D) a protein having the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4;
- (E) a protein having an amino acid sequence resulting from deletion, substitution, insertion, and/or addition of 1 to 50 amino acids in the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4, and having an activity to catalyze reaction(s) shown in the formula (III) and/or the formula (IV):
- (F) a protein having an amino acid sequence with not less than 85% identity with the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4, and having an activity to catalyze reaction(s) shown in the formula (III) and/or the formula (IV).
20 more elements
A method for producing a compound represented by the formula (2):
- comprising bringing a carbon-carbon double bond reductase enzyme, a microorganism or cell having an ability to produce the carbon-carbon double bond reductase enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the carbon-carbon double bond reductase enzyme which is obtained by culturing the microorganism or cell into contact with a compound represented by the formula (1):
- to obtain the compound represented by the formula (2);
- wherein:
- the carbon-carbon double bond reductase enzyme comprises a protein shown in the following (A), (B), or (C):
- (A) a protein having the amino acid sequence shown in SEQ ID NO:
- 1;
- (B) a protein having an amino acid sequence resulting from deletion, substitution, insertion, and/or addition of 1 to 50 amino acids in the amino acid sequence shown in SEQ ID NO:
- 1, and having an activity to catalyze reaction(s) shown in the formula (I) and/or the formula (II):
- (C) a protein having an amino acid sequence with not less than 85% identity with the amino acid sequence shown in SEQ ID NO:
- 1, having at least one amino acid substitution selected from the following groups (i) and (ii) introduced thereinto, and having an activity to catalyze reaction(s) shown in the formula (I) and/or the formula (II):
- (i) substitution of the 26th cysteine in the amino acid sequence shown in SEQ ID NO:
- 1 with an amino acid other than aspartic acid, phenylalanine, tryptophan, and tyrosine,
- (ii) substitution of the 104th alanine in the amino acid sequence shown in SEQ ID NO:
- 1 with an amino acid other than alanine.
11 more elements
A method for producing a compound represented by the formula (4):
- comprising bringing a carbonyl reductase enzyme, a microorganism or cell having an ability to produce the carbonyl reductase enzyme, a processed product of the microorganism or cell, and/or a culture solution containing the carbonyl reductase enzyme which is obtained by culturing the microorganism or cell into contact with a compound represented by the formula (1):
- to obtain the compound represented by the formula (4);
- wherein the carbonyl reductase enzyme comprises a protein shown in the following (A), (B), or (C):
- (A) a protein having the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4;
- (B) a protein having an amino acid sequence resulting from deletion, substitution, insertion, and/or addition of 1 to 50 amino acids in the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4, and having an activity to catalyze reaction(s) shown in the formula (III) and/or the formula (IV):
- (C) a protein having an amino acid sequence with not less than 85% identity with the amino acid sequence shown in SEQ ID NOS:
- 2, 3, or 4, and having an activity to catalyze reaction(s) shown in the formula (III) and/or the formula (IV).
6 more elements
Dependencies are inferred from the claim text.