Synthesis and Structural Studies of/-Peptides Derived from Fused Furano-pyran -Amino Acid and L-Ala

被引：13

作者：

Sharma, Gangavaram V. M. ^{[1
]}

Sridhar, Tailor ^{[1
]}

Reddy, Pothula Purushotham ^{[2
]}

Kunwar, Ajit C. ^{[2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, CNMR&SC, Hyderabad 500007, Andhra Pradesh, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 17期

关键词：

Protein folding; Helical structures; Conformation analysis; Peptidomimetics; Protein modificaions; ALPHA/BETA-PEPTIDES; BETA-PEPTIDES; SECONDARY STRUCTURES; FOLDAMERS; DESIGN; HELICES; PROTEIN; TURNS; CHEMISTRY; SPECTRA;

D O I：

10.1002/ejoc.201300055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New fused cis- and trans-furano-pyran -amino acids were synthesized. The cis-monomer was utilized for the synthesis of /-peptides (tetra-, penta-, hexa- and hepta-mers), to understand its impact on helix formation. Conformational analysis of the peptides with a -- sequence at the C-terminus showed the presence of a left-handed 9/11-helix in which the nine-membered H-bond motif is found to be weak and contributes only a small amount of electrostatic interaction to helix stabilization. Peptides with an -- sequence at the C-terminus revealed the presence of a left-handed 9/11-helix involving the central residues and display a clear 12-membered turn at the C-terminus. In both the cases, the 9/11-helix was stabilized by a seven-membered H-bond at the N-terminus.

引用

页码：3543 / 3554

页数：12

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