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Highly regioselective and efficient production of 1‐cyanocyclohexaneacetamide by Rhodococcus aetherivorans ZJB1208 nitrile hydratase
Author(s) -
Zheng RenChao,
Yin XinJian,
Zheng YuGuo
Publication year - 2016
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.4724
Subject(s) - nitrile hydratase , regioselectivity , alicyclic compound , nitrile , chemistry , rhodococcus , biotransformation , substrate (aquarium) , biocatalysis , organic chemistry , bioprocess , yield (engineering) , catalysis , reaction mechanism , chemical engineering , enzyme , materials science , oceanography , engineering , metallurgy , geology
BACKGROUND The regioselective hydration of alicyclic α,ω‐dinitrile 1‐cyanocyclohexaneacetonitrile (1‐ CCHAN ), followed by hydrogenation of ω‐cyano group is a green and elegant route to gabapentin. As the selective chemical hydration of dinitrile is virtually impossible, a bioprocess for regioselective hydration of 1‐ CCHAN was developed using microbial nitrile hydratase. RESULTS A newly isolated NHase producing strain, Rhodococcus aetherivorans ZJB1208 , was successfully used for hydration of 1‐ CCHAN . Some key parameters of the biocatalytic process, including reaction temperature, pH , catalyst loading and substrate loading, were optimized. The fed‐batch biotransformation was performed in non‐buffered water system with the continuous precipitation of 1‐cyanocyclohexaneacetamide. The substrate loading was increased up to 864 g L −1 (6.0 mol L −1 ), giving a product concentration of 966.7 g L −1 and biocatalyst yield (g product /g cat ) of 204.2. CONCLUSION This study is the first example of microbial nitrile hydratase with both excellent regioselectivity and strong substrate tolerance for alicyclic dinitrile and affords a potentially industrial route to gabapentin. © 2015 Society of Chemical Industry