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Solid-phase synthesis of a type II′ β-turn peptido-mimetic library

✍ Scribed by John H Grimes Jr.; Yvonne M Angell; Wayne D Kohn

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
116 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The solid-phase synthesis of a dipeptide derived 2-amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate system (IBTM) is described. The IBTM moiety is formed via a solid-phase mediated Pictet-Spengler reaction of N-terminal tryptophan and the 4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl (Dmab) ester of Fmoc protected aspartic acid b-aldehyde followed by g-lactamization. This synthesis allows the regio-and stereoselective incorporation of a dipeptide surrogate of type II% b-turns. The procedure is easily adaptable to combinatorial synthesis and a 576-member library was synthesized.

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