Synthesis and conformational studies of gamma-aminoxy peptides |
| |
Authors: | Chen Fei Song Ke-Sheng Wu Yun-Dong Yang Dan |
| |
Affiliation: | Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, People's Republic of China. |
| |
Abstract: | We have synthesized a series of gamma-aminoxy acids, including unsubstituted and gamma4-Ph-, gamma4-alkyl-, and gamma(3,4)-cyclohexyl-substituted systems. Coupling of these monomers to oligomers can be realized using EDCI/HOBt (or HOAt) as the coupling agent. gamma-Aminoxy peptides can form 10-membered-ring intramolecular hydrogen bonds-so-called "gamma N-O turns"-between adjacent residues, the extent of which is controlled by the nature of the side chain of each gamma-aminoxy acid residue, increasing from the unsubstituted gamma-aminoxy peptide to the gamma4-alkyl aminoxy peptides to the gamma4-phenyl- and gamma(3,4)-cyclohexyl-substituted aminoxy peptides. The presence of two consecutive homochiral 10-membered-ring intramolecular hydrogen bonds leads to the formation of a novel helical structure. Theoretical studies on a series of model peptides rationalize very well the experimentally observed conformational features of these gamma-aminoxy peptides. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|