Conformational studies of the linear homooligomers of a glucosederived furanoid sugar amino acid

被引：19

作者：

Chakraborty, TK ^{[1
]}

Srinivasu, P ^{[1
]}

Madhavendra, SS ^{[1
]}

Kumar, SK ^{[1
]}

Kunwar, AC ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 18期

关键词：

sugar amino acids; oligomer; hydrogen bonding; conformation; NMR;

D O I：

10.1016/j.tetlet.2004.03.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformational analysis of the linear tetramer of the glucose-derived furanoid sugar amino acid 1 by NMR and constrained molecular dynamics studies revealed that the fully protected tetramer 2a has a well-defined structure in CDCl3 with repeating P-turns, each involving a 10-membered ring structure with intramolecular hydrogen bonds between NHi --> C=Oi-2. Its deprotected versions 2b and 2c showed aggregation in organic solvents with structures similar to that of 2a. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3573 / 3577

页数：5

共 43 条

[11] Foldamers: A manifesto [J].

Gellman, SH .

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

[12]

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

[13]

2-U

[14] Carbohydrate-based mimetics in drug design: Sugar amino acids and carbohydrate scaffolds [J].

Gruner, SAW ;

Locardi, E ;

Lohof, E ;

Kessler, H .

CHEMICAL REVIEWS, 2002, 102 (02) :491-514

[15] 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

[16] A field guide to foldamers [J].

Hill, DJ ;

Mio, MJ ;

Prince, RB ;

Hughes, TS ;

Moore, JS .

CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011

[17] Tetrahydrofuran amino acids:: β- and γ-azidotetrahydrofurancarboxylic acid monomers derived from D-glucoheptonolactone as building blocks for β- and γ-oligopeptides [J].

Hungerford, NL ;

Fleet, GWJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3680-3685

[18] Tetrahydrofuran amino acids:: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid [J].

Hungerford, NL ;

Claridge, TDW ;

Watterson, MP ;

Aplin, RT ;

Moreno, A ;

Fleet, GWJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3666-3679

[19] Towards hydroxylated nylon 6: oligomers from a protected 6-amino-6-deoxy-D-allonate [J].

Hunter, DFA ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2003, 14 (24) :3831-3839

[20] Designing polymers that mimic biomolecules [J].

Kirshenbaum, K ;

Zuckermann, RN ;

Dill, KA .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1999, 9 (04) :530-535

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