Patent ID: 6756216
Filing Date: 2004-06-29
Classification: C07D,C12P,Y10S

Abstract:
A process for producing non-proteinogenic L-amino acids by direct fermentation of a microorganism strain having a deregulated cysteine metabolism in a manner which comprises,during the fermentation, adding a nucleophilic compound to a fermentation batch in amounts such that this leads to the production of non-proteinogenic L-amino acids by the microorganism strain; wherein the nucleophilic compound is added selected from the following group consisting of: thiol of the general formula (1): Hâ€”Sâ€”R1,â€ƒâ€ƒ(1) â€ƒwhere R1 is monovalent substituted or unsubstituted alkyl, alkoxy, aryl or heteroaryl radical having a maximum of 15 carbon atoms; azole of the general formula (2) or (3): â€ƒand their esters, ethers or salts, where X and Y are identical or different and X and Y denote CR4 or N, with proviso that at least one of X or Y is N, and R4 is â€”H, â€”COOH, â€”OH, â€”NH2, â€”NO2, â€”SH, â€”SO3, â€”F, â€”Cl, â€”Br, â€”I, C1-C5-alkylcarbonyl- or R1, and R1 has the meaning where R1 is monovalent substituted or unsubstituted alkyl, alkoxy, aryl or heteroaryl radical having a maximum of 15 carbon atoms; where R2 and R3 are identical or different and are R4 and R4 is â€”H, â€”COOH, â€”OH, â€”NH2, â€”NO2, â€”SH, â€”SO3, â€”F, â€”Cl, â€”Br, â€”I, C1-C5-alkylcarbonyl- or R1, and R1 has the meaning specified above; or where C1 and C2 in formula (3), instead of the substituents R2 and R3 are linked by means of a bridge [â€”CR5R6â€”]a, where a is 1, 2, 3 or 4, to form a ring, where R5 and R6 are identical or different and are R4 and R4 is â€”H, â€”COOH, â€”OH, â€”NH2, â€”NO2âˆ’, â€”SH, â€”SO3, â€”F, â€”Cl, â€”Br, â€”I, C1-C5-alkylcarbonyl or R1, and R1 has the meaning where R1 is monovalent substituted or unsubstituted alkyl, alkoxy, aryl or heteroaryl radical having a maximum of 15 carbon atoms; one or more non-adjacent groups [â€”CR5R6â€”] can be replaced by oxygen, sulfur, or an imino radical, which may be unsubstituted or substituted by C1-C5-alkyl, and two adjacent groups [â€”CR5R6â€”] can be replaced by a group [â€”CR5&boxH;CR6â€”] or by a group [â€”CR5&boxH;Nâ€”]; isoxazolinone of the general formula (4) or (5): â€ƒand their esters, ethers or salts, where X, R1, R2, R3 have the meaning where X is CR4 or N, and R4 is â€”H, â€”COOH, â€”OH, â€”NH2, â€”NO2, â€”SH, â€”SO3âˆ’, â€”F, â€”Cl, â€”Br, â€”I, C1-C5-alkylcarbonyl- or R1, and R1 has the meaning where R1 is monovalent substituted or unsubstituted alkyl, alkoxy, aryl or heteroaryl radical having a maximum of 15 carbon atoms; and where R2 and R3 are identical or different and are R4, where C1 and C2 in formula (5), instead of the substituents R2 and R3, can be linked by means of a bridge defined as for formula (3) to form a ring.