Absence of secondary structure in a carbopeptoid tetramer of a trans-5-aminomethyl-tetrahydrofuran-2-carboxylate

被引:41
作者
Smith, MD
Long, DD
Martín, A
Marquess, DG
Claridge, TDW
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)00109-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Whereas trimers and tetramers of beta-C-D-arabinofuranosyl carbohydrate amino acids adopt well defined conformations based around a repealing beta-turn like structure, stabilised by (i, i-2) inter-residue hydrogen bonds, there is no indication of any secondary structure in the tetramer of the epimeric alpha-C-D-arabinoluranosyl carbohydrate amino acid, where the C-2 and C-5 substituents of the tetrahydrofuran ring are Irans to each other. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2191 / 2194
页数:4
相关论文
共 32 条
[1]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[2]   beta-peptide foldamers: Robust Helix formation in a new family of beta-amino acid oligomers [J].
Appella, DH ;
Christianson, LA ;
Karle, IL ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13071-13072
[3]   NMR determination of the major solution conformation of a peptoid pentamer with chiral side chains [J].
Armand, P ;
Kirshenbaum, K ;
Goldsmith, RA ;
Farr-Jones, S ;
Barron, AE ;
Truong, KTV ;
Dill, KA ;
Mierke, DF ;
Cohen, FE ;
Zuckermann, RN ;
Bradley, EK .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (08) :4309-4314
[4]   POTENT INHIBITION OF GLYCOGEN-PHOSPHORYLASE BY A SPIROHYDANTOIN OF GLUCOPYRANOSE - FIRST PYRANOSE ANALOGS OF HYDANTOCIDIN [J].
BICHARD, CJF ;
MITCHELL, EP ;
WORMALD, MR ;
WATSON, KA ;
JOHNSON, LN ;
ZOGRAPHOS, SE ;
KOUTRA, DD ;
OIKONOMAKOS, NG ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1995, 36 (12) :2145-2148
[5]   THE RING CONTRACTION OF DELTA-LACTONES WITH LEAVING GROUP ALPHA-SUBSTITUENTS - A STRATEGY FOR THE SYNTHESIS OF 2,5-DISUBSTITUTED HIGHLY FUNCTIONALIZED HOMOCHIRAL TETRAHYDROFURANS [J].
CHOI, SMS ;
MYERSCOUGH, PM ;
FAIRBANKS, AJ ;
SKEAD, BM ;
BICHARD, CJF ;
MANTELL, SJ ;
SON, JC ;
FLEET, GWJ ;
SAUNDERS, J ;
BROWN, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (21) :1605-1607
[6]   An octameric carbopeptoid; Secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates [J].
Claridge, TDW ;
Long, DD ;
Hungerford, NL ;
Aplin, RT ;
Smith, MD ;
Marquess, DG ;
Fleet, GWJ .
TETRAHEDRON LETTERS, 1999, 40 (11) :2199-2202
[7]   A NEW SYNTHESIS OF N-ACETYLNEURAMINIC ACID [J].
CSUK, R ;
HUGENER, M ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1988, 71 (03) :609-618
[8]  
DULINA A, 1998, J ORG CHEM, V63, P2802
[9]   Synthesis of tetrahydropyrans from sugar lactones [J].
Estevez, JC ;
Fairbanks, AJ ;
Fleet, GWJ .
TETRAHEDRON, 1998, 54 (44) :13591-13620
[10]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180