Formation of a stable 14-helix in short oligomers of furanoid cis-β-sugar-amino acid'

被引：57

作者：

Chandrasekhar, S ^{[1
]}

Reddy, MS

Jagadeesh, B

Prabhakar, A

Rao, MHVR

Jagannadh, B

机构：

[1] Indian Inst Chem Technol, Div Organ Chem Sci, Hyderabad 500007, Andhra Pradesh, India

[2] Indian Inst Chem Technol, NMR Grp, Hyderabad 500007, Andhra Pradesh, India

[3] Indian Inst Chem Technol, Mol Modeling Grp, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 42期

关键词：

D O I：

10.1021/ja0467667

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oligomers of a new class of sugar amino acids (SAA) using a xylofuranoic acid has been shown to generate a robust 14-helix. The design involved the use of xylofuranose with a cis arrangement between the amine and carboxyl groups to promote the adoption of a 14-helix instead of a mixed 12/10-helix observed in a sugar oligomer using a ribofuranoic acid and β-Ala. The observation of a stable right-handed 14-helix in a cis-SAA is unprecedented. Copyright © 2004 American Chemical Society.

引用

页码：13586 / 13587

页数：2

共 20 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] Theoretical and experimental circular dichroic spectra of the novel helical foldamer poly[(1R,2R)-trans-2-aminocyclopentanecarboxylic acid] [J].

Applequist, J ;

Bode, KA ;

Appella, DH ;

Christianson, LA ;

Gellman, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4891-4892

[3]

AUSTIN GN, 1987, TETRAHEDRON, V43, P3095

[4]

BANERJEE A, 1997, CURR SCI, V73, P106

[5] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[6] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[7] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

[8]

Gruner SAW, 2002, CHEM-EUR J, V8, P4366, DOI 10.1002/1521-3765(20021004)8:19<4365::AID-CHEM4365>3.0.CO

[9]

2-U

[10] Sugar amino acid containing somatostatin analogues that induce apoptosis in both drug-sensitive and multidrug-resistant tumor cells [J].

Gruner, SAW ;

Kéri, G ;

Schwab, R ;

Venetianer, A ;

Kessler, H .

ORGANIC LETTERS, 2001, 3 (23) :3723-3725

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