Synthesis of a 'twisted' transition-state analogue of biotin

被引：3
|
作者：
Grant, AS [1 ]
Chaudhary, K
Stewart, L
Peters, A
Delisle, S
Decken, A
机构：
[1] Mt Allison Univ, Dept Chem, Sackville, NB E4L 1G8, Canada
[2] Univ Winnipeg, Dept Chem, Winnipeg, MB R3B 2E9, Canada
[3] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 6E2, Canada
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 08期
基金：
加拿大自然科学与工程研究理事会;
关键词：
organic synthesis; bioorganic;
D O I：
10.1016/j.tetlet.2003.12.087
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile, racemic synthesis of a 'twisted' transition-state analogue of biotin is described. A key reaction is the electronically assisted ring-closure of the sulfur containing ring by displacement of an in situ generated mesylate by a suitably positioned 4-methoxybenzyl sulfide. The crystal structure of tricyclic compound 6 shows the AB ring system to indeed be twisted. The 'twist' was introduced to examine the possible involvement of sulfur participation in biotin biochemistry. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1777 / 1780
页数：4
相关论文
共 50 条
  • [21] TWISTED ALPHA-KETO AMIDES AS TRANSITION-STATE ANALOGS FOR ACYL-TRANSFER REACTIONS - SYNTHESIS OF THE IMMUNOCONJUGATES
    YLIKAUHALUOMA, JT
    JANDA, KD
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 421 - ORGN
  • [22] Decreased Transition-State Analogue Affinity in Isotopically Heavy MTAN with Increased Catalysis
    Brown, Morais
    Schramm, Vern L.
    [J]. BIOCHEMISTRY, 2023, 62 (20) : 2928 - 2933
  • [23] Sialidase-Catalyzed One-Pot Multienzyme (OPME) Synthesis of Sialidase Transition-State Analogue Inhibitors
    Xiao, An
    Li, Yanhong
    Li, Xixuan
    Santra, Abhishek
    Yu, Hai
    Li, Wanqing
    Chen, Xi
    [J]. ACS CATALYSIS, 2018, 8 (01): : 43 - 47
  • [24] The 2.0 Å structure of malarial purine phosphoribosyltransferase in complex with a transition-state analogue inhibitor
    Shi, WX
    Li, CM
    Tyler, PC
    Furneaux, RH
    Cahill, SM
    Girvin, ME
    Grubmeyer, C
    Schramm, VL
    Almo, SC
    [J]. BIOCHEMISTRY, 1999, 38 (31) : 9872 - 9880
  • [25] Structure of the complex of bovine pancreatic phospholipase A2 with a transition-state analogue
    Sekar, K
    Kumar, A
    Liu, XH
    Tsai, MD
    Gelb, MH
    Sundaralingam, M
    [J]. ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 1998, 54 : 334 - 341
  • [26] Targeting the polyamine pathway with transition-state analogue inhibitors of 5′-methylthioadenosine phosphorylase
    Evans, GB
    Furneaux, RH
    Schramm, VL
    Singh, V
    Tyler, PC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) : 3275 - 3281
  • [27] Phosphate Binding in PNP Alters Transition-State Analogue Affinity and Subunit Cooperativity
    Minnow, Yacoba V. T.
    Schramm, Vern L.
    Almo, Steven C.
    Ghosh, Agnidipta
    [J]. BIOCHEMISTRY, 2023, 62 (21) : 3116 - 3125
  • [28] A transition-state analogue reduces protein dynamics in hypoxanthine-guanine phosphoribosyltransferase
    Wang, F
    Shi, WX
    Nieves, E
    Angeletti, RH
    Schramm, VL
    Grubmeyer, C
    [J]. BIOCHEMISTRY, 2001, 40 (27) : 8043 - 8054
  • [29] Transition-state analogue inhibitors of γ-secretase bind directly to presenilin-1
    William P. Esler
    W. Taylor Kimberly
    Beth L. Ostaszewski
    Thekla S. Diehl
    Chad L. Moore
    Jui-Yi Tsai
    Talat Rahmati
    Weiming Xia
    Dennis J. Selkoe
    Michael S. Wolfe
    [J]. Nature Cell Biology, 2000, 2 : 428 - 434
  • [30] N-Glycosyl phosphonamidates:: potential transition-state analogue inhibitors of glycopeptidases
    Ferro, V
    Weiler, L
    Withers, SG
    Ziltener, H
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (03): : 313 - 318
12345