Producing amines and diamines from a carboxylic acid or dicarboxylic acid or a monoester thereof
View Patent ↗The invention relates to a whole-cell catalyst which expresses a recombinant α-dioxygenase or the combination of a recombinant fatty acid reductase and a phosphopantetheinyl transferase which phosphopantetheinylates the fatty acid reductase, and which expresses, in addition to the α-dioxygenase and/or the combination of fatty acid reductase and phosphopantetheinyl transferase, a transaminase, wherein the phosphopantetheinyl transferase and/or transaminase is preferably recombinant; and also to a process for converting a carboxylic acid or dicarboxylic acid or a monoester thereof to an amine or diamine, comprising the steps of contacting the carboxylic acid or dicarboxylic acid or the monoester thereof with a phosphopantetheinylated fatty acid reductase or an α-dioxygenase and contacting the product with a transaminase.
1. A whole-cell catalyst, comprising heterologous expression of: a combination of a recombinant fatty acid reductase and a phosphopantetheinyl transferase capable of phosphopantetheinylating the fatty acid reductase; and a transaminase, wherein the recombinant fatty acid reductase and the phosphopantetheinyl transferase, and the transaminase, are expressed in the whole-cell catalyst, and wherein the whole-cell catalyst is a microorganism.
2. The whole-cell catalyst according to claim 1 , further comprising:
an amino acid dehydrogenase expressed in the whole-cell catalyst.
3. The whole-cell catalyst according to claim 1 , further comprising:
an alkane hydroxylase expressed in the whole-cell catalyst.
4. The whole-cell catalyst according to claim 1 , further comprising:
a polypeptide of the AlkL family expressed in the whole-cell catalyst.
5. The whole-cell catalyst according to claim 1 , further comprising:
an alcohol dehydrogenase expressed in the whole-cell catalyst.
6. The whole-cell catalyst according to claim 1 , wherein an activity of at least one enzyme involved in β-oxidation is reduced as compared to an activity of the at least one enzyme in the wild type of the whole-cell catalyst.
7. The whole-cell catalyst according to claim 1 , wherein an activity of BioH is reduced or elevated as compared to an activity of BioH in the wild type of the whole-cell catalyst.
8. The whole-cell catalyst according to claim 1 , wherein an activity of FadL is elevated as compared to an activity of FadL in the wild type of the whole-cell catalyst.
9. A reaction mixture, comprising:
the whole-cell catalyst according to claim 1 in an aqueous solution; and
a carboxylic acid, a dicarboxylic acid, or a monoester thereof having the formula (I):
R 1 -A-COOR 2 (I),
wherein R 1 is —H or COOR 3 ,
R 2 and R 3 are each independently selected from the group consisting of H, methyl, ethyl and propyl, with the proviso that at least one of the radicals R 2 and R 3 is H, and
A is an unbranched, branched, linear, cyclic, substituted or unsubstituted hydrocarbon group having at least four carbons.
10. The whole-cell catalyst according to claim 1 , wherein at least one of the phosphopantetheinyl transferase and the transaminase is recombinant.
11. The whole-cell catalyst according to claim 1 , further comprising:
at least one of a recombinant amino acid dehydrogenase, a recombinant alkane hydroxylase, a recombinant polypeptide of the AlkL family, and a recombinant alcohol dehydrogenase, expressed in the whole-cell catalyst.
12. The whole-cell catalyst according to claim 1 , wherein the recombinant fatty acid reductase is encoded by a gene having at least 70% sequence identity to the nucleotide sequence of SEQ ID NO: 1, the phosphopantetheinyl transferase is encoded by a gene having at least 70% sequence identity to the nucleotide sequence of SEQ ID NO: 2, and the transaminase is encoded by a gene having at least 70% sequence identity to the nucleotide sequence of SEQ ID NO: 12.
13. The whole-cell catalyst according to claim 1 , further comprising: an alanine dehydrogenase expressed in the whole-cell catalyst and having at least 95% sequence identity to the nucleotide sequence of SEQ ID NO: 11, wherein the recombinant fatty acid reductase is encoded by a gene having at least 95% sequence identity to the nucleotide sequence of SEQ ID NO: 1, the phosphopantetheinyl transferase is encoded by a gene having at least 95% sequence identity to the nucleotide sequence of SEQ ID NO: 2, and the transaminase is encoded by a gene having at least 95% sequence identity to the nucleotide sequence of SEQ ID NO: 12.