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
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
收藏
页码:3573 / 3577
页数:5
相关论文
共 43 条
[1]  
[Anonymous], 2018, Protein nmr spectroscopy: principles and practice
[2]   Bioinspired polymeric materials: in-between proteins and plastics [J].
Barron, AE ;
Zuckermann, RN .
CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (06) :681-687
[3]   Tetrahydrofuran amino acids -: versatile building blocks for unnatural biopolymers:: lack of secondary structure in oligomeric carbopeptoids derived from a D-galacto-5-(aminomethyl) tetrahydrofuran-2-carboxylic acid [J].
Brittain, DEA ;
Watterson, MP ;
Claridge, TDW ;
Smith, MD ;
Fleet, GWJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21) :3655-3665
[4]   Synthesis and structure of preorganized, C3-symmetric trilactam scaffolds with convergently oriented (S)-acetylthiomethyl appendages [J].
Campbell, JE ;
Englund, EE ;
Burke, SD .
ORGANIC LETTERS, 2002, 4 (13) :2273-2275
[5]   Cyclic homooligomers of furanoid sugar amino acids [J].
Chakraborty, TK ;
Srinivasu, P ;
Bikshapathy, E ;
Nagaraj, R ;
Vairamani, M ;
Kumar, SK ;
Kunwar, AC .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6257-6263
[6]  
Chakraborty TK, 2002, COMB CHEM HIGH T SCR, V5, P373
[7]   Sugar amino acids and their uses in designing bioactive molecules [J].
Chakraborty, TK ;
Ghosh, S ;
Jayaprakash, S .
CURRENT MEDICINAL CHEMISTRY, 2002, 9 (04) :421-435
[8]   Synthesis and structural studies of oligomers of 6-amino-2,5-anhydro-6-deoxy-D-mannonic acid [J].
Chakraborty, TK ;
Jayaprakash, S ;
Srinivasu, P ;
Chary, MG ;
Diwan, PV ;
Nagaraj, R ;
Sankar, AR ;
Kunwar, AC .
TETRAHEDRON LETTERS, 2000, 41 (42) :8167-8171
[9]   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
[10]   Fundamentals in the design of molecular electronic devices: Long-range charge carrier transport and electronic coupling [J].
Fox, MA .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (03) :201-207