Hydrogen bond-stabilized helix formation of a m-phenylene ethynylene oligomer

被引:70
作者
Cary, JM
Moore, JS
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[2] Univ Illinois, Dept Mat Sci & Engn, Urbana, IL 61801 USA
关键词
D O I
10.1021/ol0270982
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Incorporation of a single hydrogen bonded beta-turn mimic in the backbone of a m-phenylene ethynylene oligomer is shown to affect the thermodynamic properties of the folding reaction. Oligomers 1 and 2 both undergo solvophobic helix formation, but hydrogen bonded oligomer 1 was found to form a more stable helix with a higher tolerance to solvent denaturation than isomeric, non-hydrogen bonded oligomer 2.
引用
收藏
页码:4663 / 4666
页数:4
相关论文
共 30 条
[1]   PRINCIPLES THAT GOVERN FOLDING OF PROTEIN CHAINS [J].
ANFINSEN, CB .
SCIENCE, 1973, 181 (4096) :223-230
[2]   Hydrogen bonding in noncovalent synthesis: selectivity and the directed organization of molecular strands [J].
Archer, EA ;
Gong, HG ;
Krische, MJ .
TETRAHEDRON, 2001, 57 (07) :1139-1159
[3]   Conformational ordering of apolar, chiral m-phenylene ethynylene oligomers [J].
Brunsveld, L ;
Prince, RB ;
Meijer, EW ;
Moore, JS .
ORGANIC LETTERS, 2000, 2 (11) :1525-1528
[4]   Synthesis and conformational analysis of optically active poly(β-peptides) [J].
Cheng, JJ ;
Deming, TJ .
MACROMOLECULES, 2001, 34 (15) :5169-5174
[5]  
de Ilarduya AM, 1999, MACROMOLECULES, V32, P3257
[6]   HELICAL CONFORMATIONS IN A POLYAMIDE OF THE NYLON-3 FAMILY [J].
FERNANDEZSANTIN, JM ;
MUNOZGUERRA, S ;
RODRIGUEZGALAN, A ;
AYMAMI, J ;
LLOVERAS, J ;
SUBIRANA, JA ;
GIRALT, E ;
PTAK, M .
MACROMOLECULES, 1987, 20 (01) :62-68
[7]  
Flory P J., PRINCIPLES POLYM CHE
[8]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[9]   Helical twist sense bias in oligo(phenylene ethynylene)s induced by an optically active flexible tether [J].
Gin, MS ;
Moore, JS .
ORGANIC LETTERS, 2000, 2 (02) :135-138
[10]   A field guide to foldamers [J].
Hill, DJ ;
Mio, MJ ;
Prince, RB ;
Hughes, TS ;
Moore, JS .
CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011