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面包酵母的立体选择性还原作用 被引量：2

Stero and Chemoselective Reduction of Ketones and Aldehydes Using Baker's Yeast
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摘要 面包酵母是一种廉价易得的实验材料 ,可将酮类化合物还原为具有高光学活性的醇 ,也可还原醛、烯烃化合物、叠氮化合物等。反应条件温和 ,操作简单 ,因此 。 A review with 18 references. Baker's yeast reduction of ketones gives the corresponding secondary alcohols in good yields with excellent optical purity under mild conditions. The reduction of aldehydes,alkenes, azide group was also reported.
作者 黄南平 钟平
机构地区 温州师范学院生物与环境科学系 温州师范学院化学系
出处 《江西科学》 2002年第1期59-62,共4页 Jiangxi Science
基金 浙江省自然科学基金资助课题 (2 0 1 0 1 5 )
关键词 面包酵母 立体选择性 还原作用 酮 醇 生化试剂 不对称还原反应 酶催化化学反应 Baker's yeast, Stereoselectivity, Reduction, Ketone, Alcohols
分类号 Q949.326.1 [生物学—植物学] O621.254.2 [理学—有机化学]
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参考文献18

  • 1[1]GILLOIS J,BUISSON D,AZERAD R and JAOUEN G.Enantioselective Microbial Reduction of Transition-metalcomplexed Aromatic Ketones [ J ].J Chem Soc,Chem,Commun,1988.1224.
  • 2[2]FUJISAWA T,HAYASHI H,and KISHIOKA Y.Enantioselective Synthesis of Optically Pure Amino Alcohol Derivatives by Yeast Reduction[J].Chem Lett,1987.129.
  • 3[3]KAYSER M M,MIHOVILOVIC M D,KEARUS J,FEICHT A,STEWART J D.Baker' s Yeast-Mediated Reductions of α-Keto Esters and an α-Keto-β-lactan.Two Routes to the Paclitaxel Side chain [ J ].J Org Chem,1999,64(18) :6603.
  • 4[4]FLOREY P,SMALLRIDGE A J,TEN A,TREWHELLA M A.Chemo-and Stereoselective Reduction of α-Cyanoketone by Baker's Yeast at Low Temperature[J].Org Lett,1999,1 (12): 1879.
  • 5[5]KREUTZ O C,SEGURA R M,RODRIGUES J R,MORAU P S.Enantionselective Bioreduction of (E)-1-Pheny1-1,2- alkanedione2- (O-methy) oxime [ J ].Tetrahedron Asymmetry,2000,11(10):2107.
  • 6[6]CUI J,TERAOKA R,EMA T,SAKAI T,VTAKA M.Highly Regio-and Enantionselective Reduction of 1-Chloro-2,4-alkanediones Using Baker' s Yeast: Effects of Organic Solvents as additives [ J ].Tetrahedron Lett,1997,38(17):3021.
  • 7[7]DAHL C,FJELDBERG M,MADSEN J.Baker's Yeast:Improving the D-Stereoselectivity in Reduction of 3-oxo Esters [J] .Tetrahedron Asymmetry,1999,10(3):551.
  • 8[8]EGRI G,KOLBERT A,BALINT J,FOGASSY E,NOVAK L,POPPE L.Baker's Yeast Mediated Stereoselective Biotransformation of 1-Acetoxy-3-aryloxypropane-2ones[J].Tetrahedron Asymmetry,1998,9(2) :271.
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同被引文献29

  • 1季一兵,陈玉英,林炳承.若干手性药物的环糊精系统毛细管区带电泳拆分[J].中国药科大学学报,1996,27(4):230-234. 被引量：3
  • 2林国强 陈耀全 陈新滋.手性合成--不对称合成及其应用[M].北京:科学出版社,2000.2-17.
  • 3Fukuit, Kawamotot, Tanaka A. Tetrahedron: enzymatic preparation of optically active silylmethanol derivatives having a stereogenic silicon atom by hydrolase-catalyzed enantioselective esterification. Asymmetry, 1994, 5 (1): 73 ～ 82.
  • 4Willner, D Mandler. Enzyme-catalysed biotransformations through photochemical regeneration of nicotinamide cofactors. Enzyme Microb.Technol., 1989, 11(8):467～483.
  • 5Yang J W, Hechavarria M T, Vignola N. Metal-free, organocatalytic asymmetric transfer hydrogenation of a, β-unsaturated aldehydes[J]. Angew Chem Int Ed Engl, 2005,44(1) :108-110.
  • 6Sehaller F, Biesgen C, Mussig C, et al. 12-Oxophytodienoate reduetase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesis[J]. Planta, 2000, 210(6) : 979-984.
  • 7Barna T M, Khan H, Bruce N,et al. Crystal structure of pentaerythritol tetranitrate reductase: 'flipped'binding geometries for steroid substrates in different redox states of theenzyme[J]. J Mol Biol,2001,310(2):433 -447.
  • 8Shimoda K, Ito D I, Izumi S. Novel reductase participation in the syn-addition of hydrogen to the C=C bond of enones in the cultured dells of Nicotiana tabacum[J]. J Chem Soc Perkin Trans 1,1996, 4:355-358.
  • 9Williams R E, Rathbone D A, Scrutton N S et al. Biotransformation of explosives by the old yellow enzyme family of flavoproteins [J]. Appl Environ Microbiol, 2004,70(6):3 566-3 574.
  • 10Muller A, Hauer B, Rosche B. Enzymatic reduction of the a, β-unsaturated carbon bond in citral[J]. J Mol Catal B Enzym, 2006,30(3) : 126 -130.

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江西科学
2002年 第1期

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