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Appl Environ Microbiol. 1990 Oct;56(10):3125-9. doi: 10.1128/aem.56.10.3125-3129.1990.
2
Purification and characterization of nitrilase responsible for the enantioselective hydrolysis from Acinetobacter sp. AK 226.
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Purification and Characterization of Benzonitrilases from Arthrobacter sp. Strain J-1.从节杆菌菌株 J-1 中分离纯化苯甲腈酶及其性质研究。
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Characterization of a nitrilase from Nocardia sp. (Rhodochrous group) N.C.I.B. 11215, using p-hydroxybenzonitrile as sole carbon source.以对羟基苯甲腈作为唯一碳源，对诺卡氏菌属（红球菌类）N.C.I.B. 11215中的一种腈水解酶进行特性鉴定。
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Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae.肺炎克雷伯菌奥泽亚种对除草剂溴苯腈的代谢
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The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences.2-芳基丙酸的代谢手性转化、处置对映体选择性及其生物学后果。
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Nitrilase of Rhodococcus rhodochrous J1. Purification and characterization.红平红球菌J1腈水解酶。纯化与特性鉴定。
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Fungal degradation of aromatic nitriles. Enzymology of C-N cleavage by Fusarium solani.真菌对芳香腈的降解。茄病镰刀菌碳氮键裂解的酶学研究。
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Microbial metabolism of aromatic nitriles. Enzymology of C-N cleavage by Nocardia sp. (Rhodochrous group) N.C.I.B. 11216.芳香腈的微生物代谢。诺卡氏菌属（红球菌类）N.C.I.B. 11216催化碳氮键裂解的酶学
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不动杆菌属菌株AK226从腈化合物生产S-(+)-布洛芬。

Production of S-(+)-ibuprofen from a nitrile compound by Acinetobacter sp. strain AK226.

作者信息

Yamamoto K, Ueno Y, Otsubo K, Kawakami K, Komatsu K

机构信息

Pharmaceutical Research and Development Department, Asahi Chemical Industry Company Ltd., Miyazaki, Japan.

出版信息

Appl Environ Microbiol. 1990 Oct;56(10):3125-9. doi: 10.1128/aem.56.10.3125-3129.1990.

DOI:10.1128/aem.56.10.3125-3129.1990
PMID:2285318
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC184909/
Abstract

S-(+)-2-(4'-Isobutylphenyl)propionic acid [S-(+)-ibuprofen] was produced from racemic 2-(4'-isobutylphenyl)propionitrile (Ibu-CN) by an isolated bacterial strain, Acinetobacter sp. strain AK226. Ammonium acetate, acetonitrile, or n-butyronitrile as a carbon source in the culture medium was effective for bacterial growth and induction of this activity. The optimum pH of the reaction was around 8.0. S-(+)-Ibuprofen formed from Ibu-CN by resting cells was present in a 95% enantiomeric excess. Acinetobacter sp. strain AK226 appeared to possess a nitrilase for Ibu-CN because 2-(4'-isobutylphenyl)propionamide was not detected in the reaction mixture and 2-(4'-isobutylphenyl)propionamide was not hydrolyzed to S-(+)-ibuprofen. Since S-(+)-ibuprofen was preferentially produced while the R enantiomer of Ibu-CN was left almost intact over the time course of the reaction, the putative nitrilase appeared to be highly specific for the S enantiomer of Ibu-CN.

摘要

通过分离得到的不动杆菌属菌株AK226，从外消旋2-(4'-异丁基苯基)丙腈（布洛芬腈）生产出S-(+)-2-(4'-异丁基苯基)丙酸[S-(+)-布洛芬]。培养基中以乙酸铵、乙腈或正丁腈作为碳源，对细菌生长和该活性的诱导有效。反应的最适pH约为8.0。由静息细胞从布洛芬腈形成的S-(+)-布洛芬对映体过量率达95%。不动杆菌属菌株AK226似乎拥有一种针对布洛芬腈的腈水解酶，因为在反应混合物中未检测到2-(4'-异丁基苯基)丙酰胺，且2-(4'-异丁基苯基)丙酰胺也未水解为S-(+)-布洛芬。由于在反应过程中S-(+)-布洛芬优先产生，而布洛芬腈的R对映体几乎保持不变，推测的腈水解酶似乎对布洛芬腈的S对映体具有高度特异性。