Ronga, L., Jamieson, A. G. , Beauregard, K., Quiniou, C., Chemtob, S. and Lubell, W. D. (2010) Insertion of multiple α-amino γ-lactam (Agl) residues into a peptide sequence by solid-phase synthesis on synphase lanterns. Biopolymers, 94(2), pp. 183-191. (doi: 10.1002/bip.21288)
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Abstract
The insertion of lactams into peptide analogs can enhance potency and improve receptor selectivity. The synthesis of lactam-bridged peptide sequences has been accomplished by a solid-phase approach on SynPhase lanterns using cyclic (R)- and (S)-oxathiazinane ester (2) to annulate the amino lactam residue onto the peptide chain. Parallel synthesis of α-amino γ-lactam analogs of the allosteric modulator of IL-1 receptor 101.10 (D-Arg-D-Tyr-D-Thr-D-Val-D-Glu-D-Leu-D-Ala: rytvela) was performed by split-mix chemistry on the lanterns. In particular, the double insertion of α-amino γ-lactams in the same peptide sequence has been accomplished by this effective method for the solid-supported combinatorial synthesis of lactam-bridged peptides. Peptides bearing an Agl residue exhibited curve shapes indicative of turn conformations in their circular dichroism spectra.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Jamieson, Professor Andrew |
Authors: | Ronga, L., Jamieson, A. G., Beauregard, K., Quiniou, C., Chemtob, S., and Lubell, W. D. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Biopolymers |
Publisher: | Wiley |
ISSN: | 0006-3525 |
ISSN (Online): | 1097-0282 |
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