ENZYME CATALYSIS IN SYNTHETIC CARBOHYDRATE-CHEMISTRY

被引:0
|
作者
DRUECKHAMMER, DG [1 ]
HENNEN, WJ [1 ]
PEDERSON, RL [1 ]
BARBAS, CF [1 ]
GAUTHERON, CM [1 ]
KRACH, T [1 ]
WONG, CH [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
来源
SYNTHESIS-STUTTGART | 1991年 / 07期
关键词
PURINE-NUCLEOSIDE PHOSPHORYLASE; N-ACETYL-2-DEOXY-D-NEURAMINIC ACID-DERIVATIVES; 3'; 5'-0-ACYLATED PYRIMIDINE NUCLEOSIDES; IRREVERSIBLE TRANS-ESTERIFICATION; SECONDARY HYDROXYL-GROUPS; RABBIT MUSCLE ALDOLASE; D-GLUCOSYL FLUORIDE; PIG-LIVER ESTERASE; ORGANIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enzymes hold great potential for asymmetric synthesis of polyhydroxy species and their chiral intermediates. This article describes recent progress in the area, including the synthesis of monosaccharides, polysaccharides, nucleosides and their analogs, derivatives, conjugates, or intermediates based on combined chemical-enzymatic reactions. Highly regio- and stereoselective reactions in aqueous solutions or organic solvents with minimim protection and deprotection are demonstrated. Major applications are illustrated for the asymmetric synthesis and modification of carbohydrates and synthons based on lipases, esterases, proteases, and dehydrogenases, the effective preparation of monosaccharide-based compounds based on aldolases, and the stereocontrolled synthesis of oligosaccharides, nucleosides and derivatives based on glycosyltransferases. New strategies for changing reversible enzymatic reactions to irreversible processes, and for cofactor regeneration are also described.
引用
收藏
页码:499 / 525
页数:27
相关论文
共 50 条
  • [41] HUDSON,C.S. CONTRIBUTION TO CARBOHYDRATE-CHEMISTRY
    JEANLOZ, RW
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 25 - CAB
  • [42] APPLICATIONS OF RECENT INNOVATIONS IN MASS-SPECTROMETRY TO CARBOHYDRATE-CHEMISTRY
    DEJONGH, DC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1978, 176 (SEP): : 49 - 49
  • [43] USE OF SELENIUM IN CARBOHYDRATE-CHEMISTRY - FORMATION OF VINYL-GLYCOSIDES
    ROLLIN, P
    BENCOMO, VV
    SINAY, P
    SYNTHESIS-STUTTGART, 1984, (02): : 134 - 135
  • [44] SOME ASPECTS OF REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE REACTIONS IN CARBOHYDRATE-CHEMISTRY
    GAREGG, PJ
    PURE AND APPLIED CHEMISTRY, 1984, 56 (07) : 845 - 858
  • [45] NEW ENZYMATIC PROTECTING GROUP TECHNIQUES FOR PEPTIDE AND CARBOHYDRATE-CHEMISTRY
    WALDMANN, H
    HEUSER, A
    BRAUN, P
    KUNZ, H
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (12): : 799 - 802
  • [46] SILYL NITRONATES IN CARBOHYDRATE-CHEMISTRY - CHAIN-EXTENSION REACTIONS
    MARTIN, OR
    KHAMIS, FE
    ELSHENAWY, HA
    RAO, SP
    TETRAHEDRON LETTERS, 1989, 30 (45) : 6139 - 6142
  • [47] DICHLOROMETHYL METHYLETHER AS A REAGENT FOR ORGANIC-SYNTHESIS AND CARBOHYDRATE-CHEMISTRY
    GROSS, H
    FARKAS, I
    BOGNAIR, R
    ZEITSCHRIFT FUR CHEMIE, 1978, 18 (06): : 201 - 210
  • [48] RING EXPANSIONS IN CARBOHYDRATE-CHEMISTRY - GEM-AZO-ACETATES
    TRONCHET, JMJ
    TRONCHET, JF
    RACHIDZADEH, F
    BARBALATREY, F
    BERNADINELLI, G
    CARBOHYDRATE RESEARCH, 1988, 181 : 97 - 114
  • [49] ORGANOMETALLIC CARBOHYDRATE-CHEMISTRY - THE REACTION OF TRANSITION-METAL NUCLEOPHILES WITH CARBOHYDRATE-DERIVATIVES
    BOZELL, JJ
    HOBERG, JO
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 42 - ORGN
  • [50] Protein-Polymer Conjugates: Advancing Enzyme Catalysis in Synthetic Chemistry
    Ouyang, Jingping
    Li, Jian
    Wu, Changzhu
    CHEMCATCHEM, 2024,