Biosynthesis of Chiral Pharmaceutical Intermediates from Furfural Catalyzed by Saccharomyces cerevisiae
Furfural, as one of significant basic organic chemicals conversed from inedible renewable resource, is more and more attractive for its derivative potential. In this paper, a biotransformation system used to synthesize the chiral pharmaceutical intermediates from furfural has been established and optimized. The commercial available bakers yeast (Saccharomyces cerevisiae) was chosen as the initial biocatalyst from which a new strain with high furfural tolerance is screened and the tolerance of the new strain to furfural has been raised for 4 fold, from 100 mM to 400 mM. The optimum condition was as follows: the fermentation should be carried out under an anaerobic environment at 35 oC. And the media were sucrose 0.59 mol/L, 0.15% NaH2PO4 in tap water. After seeding of 5% (w/v) biocatalyst, the strain should be cultured for 1 h to let the cell grow freely and rapidly, then adding the substrate furfural to 2% to start the biotransformation. During the process, mainly three products had been generated: furfuryl alcohol (FA), (1R)-1-furan-2-yl-1-hydroxypropan-2-one (L-FAC), and (1S, 2S)-1-furan-2-yl propane-1,2-diol (FPG), while (2S)-1-furan-2-yl-2-hydroxypropan-1-one and (2S)-1,2- difuran-2-yl-2-hydroxyethanone are also be identified by GC/MS analysis, but the quantities are quite limited. Composition of the products mixture was variable depend upon the length of the fermentation time: the concentration of L-FAC was maximized after 4 hours, raised to 27.58% (GC area), and then decreased generally to 11.93% (GC area) after 20 hours, while the concentration of FPG raised simultaneously from 10.74% (GC area) to 25.04% (GC area). The conversion of furfural has been almost completed after 4h: up to 99.9%, and the ratio of chiral product, L-FAC + FPG, to non-chiral product, FA, has reached to 38.32: 59.09. For biotransformation of furfural to L-FAC, 4h is enough, and if the desired product is FPG, prolong the biotransformation time to 20h is better.
Bakersyeast Biotransformation Furfural (1R)-1-furan-2-yl-1-hydroxypropan-2-one (1S 2S)-1-furan-2-yl propane-1 2-diol
TANG Luhong WANG Qi WANG Ruirui CHEN Wei DENG Chao
School of Medcine and Pharmaceutics, Jiangnan University, 214122 Wuxi, China
国际会议
The 12th Asian Pacific Confederation of Chemical Engineering Congress(第十二届亚太化工联盟大会暨化工展览会)
大连
英文
2008-08-04（万方平台首次上网日期，不代表论文的发表时间）