The all-photochemical synthesis of an OGP(10–14) precursor?

Chemical Science Pub Date: 2011-10-06 DOI: 10.1039/C1SC00700A

Abstract

An all-photochemical synthesis of OGP(10–14), the biologically active part of an osteogenic growth peptide, was performed. This required the preparation of photochemically activable amino acids containing a 5,7-dinitroindoline derivative on the C-terminus and a photolabile Ddz protecting group on the N-terminus. The photochemical acyl transfer from the dinitroindoline to an incoming nucleophilic amino group, which creates the amide bond, requires an irradiation wavelength of 385 nm. The deprotection of the Ddz group requires a shorter wavelength (300 nm), thus making both successive processes compatible.

Graphical abstract: The all-photochemical synthesis of an OGP(10–14) precursor
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