Tetrahedron

Approaches to the synthesis of endothiopeptides: Synthesis of a thioamide-containing C-terminal bombesin nonapeptide

J Jurayj, M Cushman

Index: Jurayj, Jurjus; Cushman, Mark Tetrahedron, 1992 , vol. 48, # 40 p. 8601 - 8614

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Citation Number: 31

Abstract

Several approaches have been investigated for the synthesis of a bombesin C-terminal nonapeptide analogue AsnGlnTrpAlaVAlGlyHisLeu-ψCSNHMet-NH2. A new activated dithioester 16 has been synthesized. Thioacylation of methionine methyl ester with 16 was always accompanied by racemization, resulting in the formation of diastereomeric mixtures of reaction products.