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Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation

Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational... The solution-phase synthesis and cyclisation of three α,β-peptoid octamers with differing side chain patterns is reported. One of these, compound C, showed a significantly greater resolution by NMR relative to the other two structurally related octamers. This observation was studied in detail by circular dichroism at a synchrotron light source to facilitate the correlation between the side chain patterns and conformational preference of these three peptoids. The X-ray crystal structure of cyclic octamer C, the first high-resolution structure for the α,β-peptoid backbone, was also obtained from methanol. Combined solid- and solution-phase studies allowed the identification of the N-2-(benzyloxy)ethyl side chain on the β-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Amino Acids Springer Journals

Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation

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References (54)

Publisher
Springer Journals
Copyright
Copyright © 2011 by Springer-Verlag
Subject
Life Sciences; Neurobiology; Proteomics; Life Sciences, general; Biochemistry, general; Biochemical Engineering; Analytical Chemistry
ISSN
0939-4451
eISSN
1438-2199
DOI
10.1007/s00726-011-0887-1
pmid
21461676
Publisher site
See Article on Publisher Site

Abstract

The solution-phase synthesis and cyclisation of three α,β-peptoid octamers with differing side chain patterns is reported. One of these, compound C, showed a significantly greater resolution by NMR relative to the other two structurally related octamers. This observation was studied in detail by circular dichroism at a synchrotron light source to facilitate the correlation between the side chain patterns and conformational preference of these three peptoids. The X-ray crystal structure of cyclic octamer C, the first high-resolution structure for the α,β-peptoid backbone, was also obtained from methanol. Combined solid- and solution-phase studies allowed the identification of the N-2-(benzyloxy)ethyl side chain on the β-residue of the heterogeneous backbone as a key structural feature driving the increased conformational stability for octamer C.

Journal

Amino AcidsSpringer Journals

Published: Apr 2, 2011

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