Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists

F Liu, A.G. Stephen, Catherine Sarah Adamson, K Gousset, M.J. Aman, E.O. Freed, R.J. Fisher, T.R. Jr Burke

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

Replacing the Pro6 in the p6Gag-derived 9-mer “P-E-P-T-A-P-P-E-E” with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides (“peptoid hydrazones”) can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted “peptoid hydrazides” affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.
Original languageEnglish
Pages (from-to)5165-5168
JournalOrganic Letters
Volume8
Issue number22
DOIs
Publication statusPublished - Oct 2006

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