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单胺氧化酶和转氨酶筛选:拟盘多毛孢属菌株CBMAI 2030对2-甲基-6-烷基哌啶的生物转化

Monoamine oxidase and transaminase screening: biotransformation of 2-methyl-6-alkylpiperidines by Neopestalotiopsis sp. CBMAI 2030.

作者信息

Costa Jonas Henrique, da Costa Bruna Zucoloto, de Angelis Derlene Attili, Marsaioli Anita Jocelyne

机构信息

Institute of Chemistry, State University of Campinas-UNICAMP, PO Box 6154, Campinas, SP, 13083-970, Brazil.

Division of Microbial Resources, Chemical, Biological and Agricultural Pluridisciplinary Research Center-CPQBA, State University of Campinas-UNICAMP, Campinas, SP, 13148-218, Brazil.

出版信息

Appl Microbiol Biotechnol. 2017 Aug;101(15):6061-6070. doi: 10.1007/s00253-017-8389-z. Epub 2017 Jun 28.

DOI:10.1007/s00253-017-8389-z
PMID:28660289
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5522522/
Abstract

High-throughput screening detected transaminases (TAs) and monoamine oxidases (MAOs) in fungi by applying a fluorogenic probe. Strains F026, F037, F041, F053, and F057 showed the highest enzymatic conversions (31, 60, 30, 40, and 32%, respectively) and where evaluated for their ability to transform piperidines. Strain F053 (Neopestalotiopsis sp. CBMAI 2030) revealed unusual enzymatic activity to deracemize 2-methyl-6-alkylpiperidines. Neopestalotiopsis sp. CBMAI 2030 was capable to convert 2-methyl-6-propylpiperidine, 2-methyl-6-butylpiperidine, and 2-methyl-6-pentylpiperidine in piperideine with 11, 14, and 24% conversion, respectively. The activity was enhanced by cultivating the fungus with 2-methyl-6-pentylpiperidine (38% conversion and 73% ee).

摘要

高通量筛选通过应用荧光探针检测真菌中的转氨酶(TAs)和单胺氧化酶(MAOs)。菌株F026、F037、F041、F053和F057表现出最高的酶促转化率(分别为31%、60%、30%、40%和32%),并对它们转化哌啶的能力进行了评估。菌株F053(新拟盘多毛孢属CBMAI 2030)显示出对2-甲基-6-烷基哌啶进行消旋化的异常酶活性。新拟盘多毛孢属CBMAI 2030能够分别将2-甲基-6-丙基哌啶、2-甲基-6-丁基哌啶和2-甲基-6-戊基哌啶转化为哌啶,转化率分别为11%、14%和24%。通过用2-甲基-6-戊基哌啶培养真菌,该活性得到增强(转化率为38%,对映体过量值为73%)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/8dfd4b7dafb7/253_2017_8389_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/f6ae3764cf45/253_2017_8389_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/9e65a4a5dd75/253_2017_8389_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/552fb97f4912/253_2017_8389_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/50e0e6ee325e/253_2017_8389_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/8dfd4b7dafb7/253_2017_8389_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/f6ae3764cf45/253_2017_8389_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/9e65a4a5dd75/253_2017_8389_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/552fb97f4912/253_2017_8389_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/50e0e6ee325e/253_2017_8389_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/baa4/5522522/8dfd4b7dafb7/253_2017_8389_Fig5_HTML.jpg

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A regio- and stereoselective ω-transaminase/monoamine oxidase cascade for the synthesis of chiral 2,5-disubstituted pyrrolidines.一种区域和立体选择性的ω-转氨酶/单胺氧化酶级联反应,用于合成手性 2,5-二取代吡咯烷。
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