Peptide synthesis by prior thiol capture. 2. Design of templates for intramolecular O, N-acyl transfer. 4, 6-Disubstituted dibenzofurans as optimal spacing elements

DS Kemp, NG Galakatos, B Bowen…

Index: Kemp, D. S.; Galakatos, Nicholas G.; Bowen, Benjamin; Tan, Kenneth Journal of Organic Chemistry, 1986 , vol. 51, # 10 p. 1829 - 1838

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Citation Number: 54

Abstract

A central feature of the strategy for amide bond formation by prior thiol capture is an intramolecular acyl transfer across a template that links the phenolic ester function of one peptide with an unsymmetrical disulfide involving the side chain of the N-terminal cysteine residue of a second peptide. The structures of 4-hydroxy-6-mercaptodibenzofuran (3) and 4- hydroxy-6-mercaptophenoxythih (4) are established by'H NMR spectra of deuterated ...