Facile synthesis of (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine, an isotype-selective agonist of metabotropic glutamate receptors

被引:29
|
作者
Ma, DW
Ma, ZC
机构
[1] Stt. Key Lab. Bio-Organ. Nat. P., Shanghai Inst. of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Lu
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(97)10037-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2S,1'S,2'S)-2-(Carboxycyclopropyl)glycine (L-CCG-I) was synthesized in 12 steps and 14% overall yield by using Sharpless's asymmetric dihydroxylation reaction and stereochemically controlled cyclopropanation as key steps. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7599 / 7602
页数:4
相关论文
共 50 条
  • [21] 2ND MESSENGER GENERATION BY THE PUTATIVE METABOTROPIC AGONIST (2S,3S,4S)-ALPHA-(CARBOXYCYCLOPROPYL)-GLYCINE IN GUINEA-PIG CEREBRAL CORTICAL SLICES
    CARTMELL, J
    ALEXANDER, SPH
    KENDALL, DA
    BRITISH JOURNAL OF PHARMACOLOGY, 1994, 111 : P68 - P68
  • [22] Anticonvulsant and glutamate release-inhibiting properties of the highly potent metabotropic glutamate receptor agonist (2S,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl) glycine (DCG-IV)
    Attwell, PJE
    Kent, NS
    Jane, DE
    Croucher, MJ
    Bradford, HF
    BRAIN RESEARCH, 1998, 805 (1-2) : 138 - 143
  • [23] Stereoselective synthesis of (2S)-2-hydroxymethylglutamic acid, a potent agonist of metabotropic glutamate receptor mGluR3
    Choudhury, PK
    Le Nguyen, BK
    Langlois, N
    TETRAHEDRON LETTERS, 2002, 43 (03) : 463 - 464
  • [24] 2,3′-disubstituted-2-(2′-carboxycyclopropyl)glycines as potent and selective antagonists of metabotropic glutamate receptors
    Collado, I
    Ezquerra, J
    Mazón, A
    Pedregal, C
    Yruretagoyena, B
    Kingston, AE
    Tomlinson, R
    Wright, RA
    Johnson, BG
    Schoepp, DD
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (20) : 2849 - 2854
  • [25] (2S,1'S,2'R,3'R)-2(2'-Carboxy-3'-hydroxymethyl-cyclopropyl)glycine-[3H], a potent and selective radioligand for labeling group 2 and 3 metabotropic glutamate receptors
    Wheeler, WJ
    Clodfelter, DK
    Kulanthaivel, P
    Pedregal, C
    Stoddard, EA
    Wright, RA
    Schoepp, DD
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (02) : 349 - 351
  • [26] Effects of L-Glutamate Transport Inhibition by a Conformationally Restricted Glutamate Analogue (2S,1'S,2'R)-2-(Carboxycyclopropyl)Glycine (L-CCG III) on Metabolism in Brain Tissue In Vitro Analysed by NMR Spectroscopy
    Charbel El-Hajj Moussa
    Ann D. Mitrovic
    Robert J. Vandenberg
    Tanya Provis
    Caroline Rae
    William A. Bubb
    Vladimir J. Balcar
    Neurochemical Research, 2002, 27 : 27 - 35
  • [27] Effects of L-glutamate transport inhibition by a conformationally restricted glutamate analogue (2S,1′S,2′R)-2-(carboxycyclopropyl)glycine (L-CCG III) on metabolism in brain tissue in vitro analysed by NMR spectroscopy
    Moussa, CEH
    Mitrovic, AD
    Vandenberg, RJ
    Provis, T
    Rae, C
    Bubb, WA
    Balcar, VJ
    NEUROCHEMICAL RESEARCH, 2002, 27 (1-2) : 27 - 35
  • [28] AGONIST ANALYSIS OF 2-(CARBOXYCYCLOPROPYL)GLYCINE ISOMERS FOR CLONED METABOTROPIC GLUTAMATE RECEPTOR SUBTYPES EXPRESSED IN CHINESE-HAMSTER OVARY CELLS
    HAYASHI, Y
    TANABE, Y
    ARAMORI, I
    MASU, M
    SHIMAMOTO, K
    OHFUNE, Y
    NAKANISHI, S
    BRITISH JOURNAL OF PHARMACOLOGY, 1992, 107 (02) : 539 - 543
  • [29] Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination
    Gu, X
    Xian, M
    Roy-Faure, S
    Bolte, J
    Aitken, DJ
    Gefflaut, T
    TETRAHEDRON LETTERS, 2006, 47 (02) : 193 - 196
  • [30] A fluoride 2-(carboxycyclopropyl) glycine derivative, F2CCG-I, as a useful pharmacological probe for elucidating the physiological roles of metabotropic glutamate receptors
    Shinozaki, H
    Ishida, M
    METABOTROPIC GLUTAMATE RECEPTORS AND BRAIN FUNCTION, 1998, 12 : 271 - 280