An octameric carbopeptoid; Secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates

被引:78
作者
Claridge, TDW
Long, DD
Hungerford, NL
Aplin, RT
Smith, MD
Marquess, DG
Fleet, GWJ
机构
[1] Oxford Ctr Mol Sci, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
[3] Adv Med Inc, San Francisco, CA 94080 USA
关键词
D O I
10.1016/S0040-4039(99)00111-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient synthesis of an octameric furanose carbopeptoid, readily purified by chromatography in ethyl acetate:hexane (2:1), is reported. Extensive NMR studies suggest that two tetrameric 5-aminomethyltetrahydrofuran-2-carboxylate are prone to adopt solution conformations reminiscent of a repeating beta-turn, a third tetramer and the corresponding octamer may tend towards a left-handed alpha-helix. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2199 / 2202
页数:4
相关论文
共 8 条
[1]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[2]   RELIABLE 2-DIMENSIONAL ROTATING-FRAME CROSS-RELAXATION MEASUREMENTS IN COUPLED SPIN SYSTEMS [J].
HWANG, TL ;
SHAKA, AJ .
JOURNAL OF MAGNETIC RESONANCE SERIES B, 1993, 102 (02) :155-165
[3]   IMPROVED RESOLUTION IN PROTON-DETECTED HETERONUCLEAR LONG-RANGE CORRELATION [J].
KESSLER, H ;
SCHMIEDER, P ;
KOCK, M ;
KURZ, M .
JOURNAL OF MAGNETIC RESONANCE, 1990, 88 (03) :615-618
[4]   From sequencamers to foldamers?: Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates [J].
Long, DD ;
Hungerford, NL ;
Smith, MD ;
Brittain, DEA ;
Marquess, DG ;
Claridge, TDW ;
Fleet, GWJ .
TETRAHEDRON LETTERS, 1999, 40 (11) :2195-2198
[5]   A solid phase approach to oligomers of carbohydrate amino-acids: Secondary structure in a trimeric furanose carbopeptoid [J].
Long, DD ;
Smith, MD ;
Marquess, DG ;
Claridge, TDW ;
Fleet, GWJ .
TETRAHEDRON LETTERS, 1998, 39 (50) :9293-9296
[6]   Absence of secondary structure in a carbopeptoid tetramer of a trans-5-aminomethyl-tetrahydrofuran-2-carboxylate [J].
Smith, MD ;
Long, DD ;
Martín, A ;
Marquess, DG ;
Claridge, TDW ;
Fleet, GWJ .
TETRAHEDRON LETTERS, 1999, 40 (11) :2191-2194
[7]   Secondary structure in oligomers of carbohydrate amino acids [J].
Smith, MD ;
Claridge, TDW ;
Tranter, GE ;
Sansom, MSP ;
Fleet, GWJ .
CHEMICAL COMMUNICATIONS, 1998, (18) :2041-2042
[8]   GRADIENT SELECTION IN INVERSE HETERONUCLEAR CORRELATION SPECTROSCOPY [J].
WILLKER, W ;
LEIBFRITZ, D ;
KERSSEBAUM, R ;
BERMEL, W .
MAGNETIC RESONANCE IN CHEMISTRY, 1993, 31 (03) :287-292