Author:
Pan Jiang,Dang Ngoc-Duy,Zheng Gao-Wei,Cheng Bo,Ye Qin,Xu Jian-He
Abstract
Abstract
Background
levo-Menthol is an important flavoring chemical, which can be prepared by enantioselective enzymatic hydrolysis of dl-menthyl esters. A recombinant esterase (BsE) cloned from Bacillus subtilis 0554 shows excellent enantioselectivity to dl-menthyl acetate and has been immobilized using cross-linked enzyme aggregates. Though BsE has relatively high substrate tolerance, the conversion of dl-menthyl acetate decreased sharply with the increase of substrate loading from 1 to 3 M in mono-aqueous system, which might be due to the severe inhibition of enzyme activity at extremely high load of substrate or product. In this work, enzymatic hydrolysis of dl-menthyl acetate with an extremely high load using the immobilized CLEA-BsE was investigated in an organic-aqueous biphasic system containing surfactant to establish a promising bioprocess for large-scale production of l-menthol.
Results
An efficient biphasic reaction system of pentanol-water containing sodium dodecyl sulfate (SDS) was developed for improving enantioselective hydrolysis of dl-menthyl acetate to produce l-menthol by immobilized BsE. Under the optimized reaction conditions, l-menthol was produced in >97% enantiomeric excess (ee) at a substrate load of up to 3.0 M with >40% conversion.
Conclusions
All the positive features demonstrate the potential applicability of the bioprocess for the large-scale production of l-menthol.
Publisher
Springer Science and Business Media LLC
Subject
Renewable Energy, Sustainability and the Environment,Biomedical Engineering,Food Science,Biotechnology
Reference32 articles.
1. Clark GS: Menthol. Perfum Flavor 1998, 23: 33–46.
2. Clark GS: Aroma chemical profile: menthol. Perfum Flavor 2007, 32: 38–47.
3. Rendler S, Auer G, Keller M, Oestreich M: Preparation of a privileged silicon-stereogenic silane: classical versus kinetic resolution. Adv Synth Catal 2006, 348: 1171–1182. 10.1002/adsc.200606071
4. Cattaruzza F, Fares V, Flamini A, Prosperi T (2006) Synthesis of enantiomeric menthol derivatives for forming and probing chiral surfaces. X-ray crystal and molecular structures of (+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcycl-ohexane. Tetrahedron-Asymmetry 17:1296–1300
5. Michael M: Hot market for a cool chemical. Chem Eng News 2010, 88: 15–16.
Cited by
12 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献