Insertion of multiple α-amino γ-lactam (Agl) residues into a peptide sequence by solid-phase synthesis on synphase lanterns

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)

Full text not currently available from Enlighten.

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
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

University Staff: Request a correction | Enlighten Editors: Update this record