Use of enzyme penicillin acylase in selective amidation/amide hydrolysis to resolve ethyl 3-amino-4-pentynoate isomers

被引:38
作者
Topgi, RS
Ng, JS
Landis, B
Wang, P
Behling, JR
机构
[1] SEARLE, Chem Sci, R&D, Skokie, IL 60077 USA
[2] Monsanto Co, Bioproc Grp, St Louis, MO 63198 USA
关键词
penicillin acylase; resolve; beta-amino acid; acylation; deacylation;
D O I
10.1016/S0968-0896(99)00155-8
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
The beta-amino acid, (S)-ethyl-3-amino-4-pentynoate: is a chiral synthon used in the synthesis of xemilofiban hydrochloride, an anti-platelet agent. A biocatalytic approach was developed to resolve (R)- and (S)-enantiomers of ethyl 3-amino-4-pentynoate in enantiomerically pure form employing the enzyme Penicillin acylase. In the acylation, phenylacetic acid was used as an acylating agent. We have shown that both the acylation and deacylation can be employed and that the activity of the enzyme Penicillin acylase can be controlled by maintaining an appropriate pH of the reaction medium. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2221 / 2229
页数:9
相关论文
共 61 条
  • [51] PREPARATION OF OPTICALLY-ACTIVE 1-AMINOALKYLPHOSPHONIC ACIDS BY STEREOSELECTIVE ENZYMATIC-HYDROLYSIS OF RACEMIC N-ACYLATED 1-AMINOALKYLPHOSPHONIC ACIDS
    SOLODENKO, VA
    KASHEVA, TN
    KUKHAR, VP
    KOZLOVA, EV
    MIRONENKO, DA
    SVEDAS, VK
    [J]. TETRAHEDRON, 1991, 47 (24) : 3989 - 3998
  • [52] BIOCATALYTIC APPROACH TO ENANTIOMERICALLY PURE BETA-AMINO ACIDS
    SOLOSHONOK, VA
    FOKINA, NA
    RYBAKOVA, AV
    SHISHKINA, IP
    GALUSHKO, SV
    SOROCHINSKY, AE
    KUKHAR, VP
    SAVCHENKO, MV
    SVEDAS, VK
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1601 - 1610
  • [53] Biomimetic transamination of α-alkyl β-keto carboxylic esters.: Chemoenzymatic approach to the stereochemically defined α-alkyl β-fluoroalkyl β-amino acids
    Soloshonok, VA
    Soloshonok, IV
    Kukhar, VP
    Svedas, VK
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) : 1878 - 1884
  • [54] Spatola A. F, 1983, CHEM BIOCH AMINO ACI, V7, P331
  • [55] ENZYMATIC-SYNTHESIS DESIGN AND ENZYMATIC-SYNTHESIS OF ASPARTAME
    STOINEVA, IB
    GALUNSKY, BP
    LOZANOV, VS
    IVANOV, IP
    PETKOV, DD
    [J]. TETRAHEDRON, 1992, 48 (06) : 1115 - 1122
  • [56] CHIRAL AUXILIARY-MEDIATED ASYMMETRIC INDUCTION IN A THERMAL INVERSE ELECTRON DEMAND HETERO-DIELS-ALDER REACTION - ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL A-RING SIDE-CHAIN
    SWINDELL, CS
    TAO, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 5889 - 5891
  • [57] CARBAMATE-DIRECTED STEREOSELECTIVE HYDROGENATION AND KINETIC RESOLUTION OF N-PROTECTED ALPHA-(ALPHA-AMINOALKYL)ACRYLATES
    TAKAGI, M
    YAMAMOTO, K
    [J]. TETRAHEDRON, 1991, 47 (42) : 8869 - 8882
  • [58] A MILD AND EFFICIENT METHOD FOR THE PREPARATION OF N-TOSYL AMIDES AND LACTAMS
    TANNER, D
    SOMFAI, P
    [J]. TETRAHEDRON, 1988, 44 (02) : 613 - 618
  • [59] WALDMANN H, 1991, KONTAKTE, V2, P33
  • [60] POTENT IN-VITRO AND IN-VIVO INHIBITORS OF PLATELET-AGGREGATION BASED UPON THE ARG-GLY-ASP SEQUENCE OF FIBRINOGEN - (AMINOBENZAMIDINO)SUCCINYL (ABAS) SERIES OF ORALLY-ACTIVE FIBRINOGEN RECEPTOR ANTAGONISTS
    ZABLOCKI, JA
    RICO, JG
    GARLAND, RB
    ROGERS, TE
    WILLIAMS, K
    SCHRETZMAN, LA
    RAO, SA
    BOVY, PR
    TJOENG, FS
    LINDMARK, RJ
    TOTH, MV
    ZUPEC, ME
    MCMACKINS, DE
    ADAMS, SP
    MIYANO, M
    MARKOS, CS
    MILTON, MN
    PAULSON, S
    HERIN, M
    JACQMIN, P
    NICHOLSON, NS
    PANZERKNODLE, SG
    HAAS, NF
    PAGE, JD
    SZALONY, JA
    TAITE, BB
    SALYERS, AK
    KING, LW
    CAMPION, JG
    FEIGEN, LP
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) : 2378 - 2394