Enantioselective synthesis of amino acid amides via enzymatic ammoniolysis of amino acid esters

被引：36
作者：
Hacking, MAPJ [1 ]
Wegman, MA [1 ]
Rops, J [1 ]
van Rantwijk, F [1 ]
Sheldon, RA [1 ]
机构：
[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands
来源：
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 1998年 / 5卷 / 1-4期
关键词：
ammoniolysis; deracemisation; Candida antarctica; lipase; D-phenylglycine amide; dynamic kinetic resolution;
D O I：
10.1016/S1381-1177(98)00025-3
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：
Ammoniolysis of D,L-phenylglycine methyl ester catalysed by Candida antarctica B lipase (Novozym 435) gave D-phenylglycine amide with 78% ee at 47% conversion. The combination of this reaction with racemisation of the unconverted ester in a single step was investigated. Pyridoxal and salicylaldehyde efficiently catalysed the racemisation of the ester. Because the solubility of the amide was law under the reactions conditions, its racemisation was slow. Ln-process racemisation of the reactant gave D-phenylglycine amide with 73% ee at 85% conversion. (C) 1998 Elsevier Science B.V. All rights reserved.
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页码：155 / 157
页数：3
相关论文
共 11 条
  • [1] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
    CHEN, CS
    FUJIMOTO, Y
    GIRDAUKAS, G
    SIH, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
  • [2] CHEN ST, 1993, SYNTHESIS-STUTTGART, P858
  • [3] Ammonolysis of carboxylic esters catalyzed by lipases - Synthesis of fatty acid amides
    De Zoete, MC
    Kock-Van Dalen, AC
    Van Rantwijk, F
    Sheldon, RA
    [J]. ENZYME ENGINEERING XIII, 1996, 799 : 346 - 350
  • [4] A NEW ENZYMATIC-REACTION - ENZYME-CATALYZED AMMONOLYSIS OF CARBOXYLIC ESTERS
    DEZOETE, MC
    KOCKVANDALEN, AC
    VANRANTWIJK, F
    SHELDON, RA
    [J]. BIOCATALYSIS, 1994, 10 (1-4): : 307 - 316
  • [5] ESTER AMMONIOLYSIS - A NEW ENZYMATIC-REACTION
    DEZOETE, MC
    DALEN, ACK
    VANRANTWIJK, F
    SHELDON, RA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (24) : 1831 - 1832
  • [6] DEZOETE MC, 1995, RECL TRAV CHIM PAY B, V114, P171
  • [7] Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides (vol 1, pg 109, 1996)
    deZoete, MC
    KockvanDalen, AC
    vanRantwijk, F
    Sheldon, RA
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1996, 2 (2-3) : 141 - 145
  • [8] Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides
    deZoete, MC
    KockvanDalen, AC
    vanRantwijk, F
    Sheldon, RA
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1996, 1 (3-6) : 109 - 113
  • [9] A new enzymatic one-pot procedure for the synthesis of carboxylic amides from carboxylic acids
    deZoete, MC
    KockvanDalen, AC
    vanRantwijk, F
    Sheldon, RA
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1996, 2 (01) : 19 - 25
  • [10] DEZOETE MC, Patent No. 07359
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