Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 21st October 2020 from 07:00 AM to 07:00 PM (BST).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 40, 2012
Previous Article Next Article

A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

Author affiliations

Abstract

Novel, efficient and mild preparation of 7- and 8-membered cyclic di- and 10-membered cyclic tripeptides containing α-, β- or γ-amino acid residues is effected by a Staudinger-mediated ring closure. Medium-sized cyclic di- and tripeptides – recognized as difficult targets – were obtained in moderate to good yields according to a straightforward sequence. Empirical force-field calculations were undertaken to determine their conformational behaviors and showed high levels of similarity with X-ray results. A computational study at the B3LYP/6-31+G** level of theory afforded information regarding the impact of the sequence, ring-size and substitution on the activation barriers for the cyclization of azido peptide thioesters.

Graphical abstract: A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

Back to tab navigation

Supplementary files

Article information


Submitted
22 May 2012
Accepted
22 Aug 2012
First published
23 Aug 2012

Org. Biomol. Chem., 2012,10, 8055-8058
Article type
Communication

A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

K. Ha, J. M. Monbaliu, B. C. Williams, G. G. Pillai, C. E. Ocampo, M. Zeller, C. V. Stevens and A. R. Katritzky, Org. Biomol. Chem., 2012, 10, 8055
DOI: 10.1039/C2OB25996F

Social activity

Search articles by author

Spotlight

Advertisements