Chemoselective biohydrogenation of α,β- and α,β,γ,δ-unsaturated ketones by the marine-derived fungus Penicillium citrinum CBMAI 1186 in a biphasic system

被引:27
|
作者
Ferreira, Irlon M. [1 ]
Meira, Eloa B. [1 ]
Rosset, Isac G. [1 ]
Porto, Andre L. M. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim Sao Carlos, Lab Quim Organ & Biocatalise, BR-13563120 Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Biocatalysis; Enoate reductases; alpha; beta-Unsaturated ketones; Marine microorganisms; WHOLE CELLS; ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC BIOREDUCTION; SELECTIVE REDUCTION; ENOATE REDUCTASES; BIOTRANSFORMATIONS; HYDROGENATION;
D O I
10.1016/j.molcatb.2015.01.017
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
To broaden the range of applicability of a reduction reaction mediated by the marine fungal strain Penicillium citrinum CBMAI 1186 to organic chemical processes, the ability of whole mycelia to grow in biphasic mixtures with organic solvents was tested with acetone, ethyl acetate, n-butanol, dichloromethane, n-hexane and toluene. n-Hexane was the least toxic solvent according to the amount of mycelial mass grown in an artificial sea water medium mixed with each solvent. Therefore, whole hyphae of P. citrinum CBMAI 1186 were used as biocatalysts in the chemoselective biotransformation of the carbon-carbon double bond in alpha,beta-, di-alpha,beta-, and mono-alpha,beta,gamma,delta-unsaturated ketones (3a, 3c-f) in a biphasic system of phosphate buffer and n-hexane (9:1). Only the di-alpha,beta,gamma,delta-unsaturated ketone (3b) was not biocatalyzed under these conditions. In general, there were good conversions of saturated ketones by the enoate reductase enzymes of P. citrinum CBMAI 1186. (C) 2015 Elsevier B.V. All rights reserved.
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页码:59 / 65
页数:7
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