Differential effects of stereochemistry and C-4 substituents on the enantioselectivity of PLE and PPL catalysed hydrolysis of 3,4-disubstituted beta-lactams

被引:22
作者
Basak, A
Mahato, T
Bhattacharya, G
Mukherjee, B
机构
[1] Department of Chemistry, Indian Institute of Technology
关键词
D O I
10.1016/S0040-4039(96)02381-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pig Liver Esterase (PLE) and Pig Pancreas Lipase (PPL) catalysed hydrolysis of (+/-)trans-3-carbethoxy and (+/-) cis-3-acetoxymethyl 4-substituted beta-lactams revealed interesting dependence on C-3, C-4 stereochemistry and nature of C-4 substituents. (C) 1997, Elsevier Science Ltd. All rights reserved.
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收藏
页码:643 / 646
页数:4
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共 13 条
  • [1] Tricarbonyl(eta(6)arene)chromium(0) complexes as chiral auxiliaries: Asymmetric synthesis of beta-aminoesters and beta-lactams by Reformatsky condensation
    Baldoli, C
    DelButtero, P
    Licandro, E
    Papagni, A
    Pilati, T
    [J]. TETRAHEDRON, 1996, 52 (13) : 4849 - 4856
  • [2] CHEMOENZYMATIC SYNTHESIS OF THE C-13 SIDE-CHAIN OF TAXOL - OPTICALLY-ACTIVE 3-HYDROXY-4-PHENYL BETA-LACTAM DERIVATIVES
    BRIEVA, R
    CRICH, JZ
    SIH, CJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1068 - 1075
  • [3] CIS-AZETIDIN-2-ONES AND TRANS-AZETIDIN-2-ONES FROM NITRONES AND COPPER ACETYLIDE
    DING, LK
    IRWIN, WJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (22): : 2382 - 2386
  • [4] DETERMINATION OF ENANTIOMERIC PURITY BY AN OPTICALLY ACTIVE NUCLEAR MAGNETIC RESONANCE SHIFT REAGENT OF WIDE APPLICABILITY
    FRASER, RR
    PETIT, MA
    SAUNDERS, JK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (22): : 1450 - &
  • [5] DILEMMA REGARDING AN ACTIVE-SITE MODEL FOR PORCINE PANCREATIC LIPASE
    HULTIN, PG
    JONES, JB
    [J]. TETRAHEDRON LETTERS, 1992, 33 (11) : 1399 - 1402
  • [6] REACTIONS OF COPPER(I) PHENYLACETYLIDE WITH NITRONES
    KINUGASA, M
    HASHIMOTO, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (08) : 466 - +
  • [7] STEREOCHEMISTRY IN BETA-LACTAM SERIES .3.
    LUCHE, JL
    KAGAN, HB
    PARTHASA.R
    TSOUCARI.G
    DERANGO, C
    ZELWER, C
    [J]. TETRAHEDRON, 1968, 24 (03) : 1275 - &
  • [8] A WATER-SOLUBLE PRODRUG OF TAXOL WITH SELF-ASSEMBLING PROPERTIES
    NICOLAOU, KC
    GUY, RK
    PITSINOS, EN
    WRASIDLO, W
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (15-16): : 1583 - 1587
  • [9] RECENT ADVANCES IN THE BETA-LACTAM SYNTHON METHOD
    OJIMA, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) : 383 - 389
  • [10] NEW AND EFFICIENT APPROACHES TO THE SEMISYNTHESIS OF TAXOL AND ITS C-13 SIDE-CHAIN ANALOGS BY MEANS OF BETA-LACTAM SYNTHON METHOD
    OJIMA, I
    HABUS, I
    ZHAO, M
    ZUCCO, M
    PARK, YH
    SUN, CM
    BRIGAUD, T
    [J]. TETRAHEDRON, 1992, 48 (34) : 6985 - 7012