From sequencamers to foldamers?: Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates

被引：61

作者：

Long, DD

Hungerford, NL

Smith, MD

Brittain, DEA

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, S San Francisco, CA 94080 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(99)00110-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of three stereoisomeric cis- and trans-5-azidomelhyl-tetrahydrofuran-2-carboxylates in which a ketal-protected cis-diol unit is present is described. The monomers undergo efficient oligomerisation to tetrameric carbopeptoids in which the diol protection facilitates ready purification by chromatography which augurs well for the formation of homogeneous higher polymers. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2195 / 2198

页数：4

共 6 条

[1] ACETONIDES OF ALPHA-HYDROXY-DELTA-ALTRONOLACTONES
BICHARD, CJF
FAIRBANKS, AJ
FLEET, GWJ
RAMSDEN, NG
VOGT, K
DOHERTY, O
PEARCE, L
WATKIN, DJ
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (09) : 901 - 912
[2] Chandran A., UNPUB
[3] An octameric carbopeptoid; Secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates
Claridge, TDW
Long, DD
Hungerford, NL
Aplin, RT
Smith, MD
Marquess, DG
Fleet, GWJ
[J]. TETRAHEDRON LETTERS, 1999, 40 (11) : 2199 - 2202
[4] SYNTHESIS OF 5-EPIHYDANTOCIDIN FROM D-RIBOSE
FAIRBANKS, AJ
FLEET, GWJ
[J]. TETRAHEDRON, 1995, 51 (13) : 3881 - 3894
[5] Foldamers: A manifesto
Gellman, SH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) : 173 - 180
[6] Absence of secondary structure in a carbopeptoid tetramer of a trans-5-aminomethyl-tetrahydrofuran-2-carboxylate
Smith, MD
Long, DD
Martín, A
Marquess, DG
Claridge, TDW
Fleet, GWJ
[J]. TETRAHEDRON LETTERS, 1999, 40 (11) : 2191 - 2194

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