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Synthesis of Imidazol-2-yl Amino Acids by Using Cells from Alkane-Oxidizing Bacteria

机译:利用烷烃氧化菌细胞合成咪唑-2-基氨基酸

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Sixty-one strains of alkane-oxidizing bacteria were tested for their ability to oxidize N-(2-hexylamino-4-phenylimidazol-1-yl)-acetamide to imidazol-2-yl amino acids applicable for pharmaceutical purposes. After growth with n-alkane, 15 strains formed different imidazol-2-yl amino acids identified by chemical structure analysis (mass and nuclear magnetic resonance spectrometry). High yields of imidazol-2-yl amino acids were produced by the strains Gordonia rubropertincta SBUG 105, Gordonia terrae SBUG 253, Nocardia asteroides SBUG 175, Rhodococcus erythropolis SBUG 251, and Rhodococcus erythropolis SBUG 254. Biotransformation occurred via oxidation of the alkyl side chain and produced 1-acetylamino-4-phenylimidazol-2-yl-6-aminohexanoic acid and the butanoic acid derivative. In addition, the acetylamino group of these products and of the substrate was transformed to an amino group. The product pattern as well as the transformation pathway of N-(2-hexylamino-4-phenylimidazol-1-yl)-acetamide differed in the various strains used.
机译:测试了六十一株烷烃氧化细菌菌株将N-(2-(2-己基氨基-4-苯基咪唑-1-基)-乙酰胺氧化为可用于制药目的的咪唑-2-基氨基酸的能力。用正构烷烃生长后,有15个菌株形成了不同的咪唑-2-基氨基酸,这些氨基酸通过化学结构分析(质谱和核磁共振光谱法)鉴定。菌株Gordonia rubropertincta SBUG 105,Gordonia terrae SBUG 253,诺卡氏小行星SBUG 175,Rhodococcus erythropolis SBUG 251和Rhodococcus erythropolis SBUG 254菌株可产生高产量的咪唑-2-基氨基酸。通过烷基链的氧化发生生物转化。制得1-乙酰氨基-4-苯基咪唑-2-基-6-氨基己酸和丁酸衍生物。另外,这些产物和底物的乙酰氨基被转化为氨基。 N-(2-(2-己基氨基-4-苯基咪唑-1-基)-乙酰胺的产物模式和转化途径在所用的各种菌株中有所不同。

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