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

Replacing the Pro6 in the p6(Gag)-derived 9-mer P-E-P-T-A-(P) under bar -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.