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N, N-diisopropyl-bis(4-chlorobenzyl) phosphoramidite: A versatile phosphitylating agent for the phosphorylation of hydroxy amino acids and preparation of protected phosphopeptides

✍ Scribed by H. B. A. de Bont; J. H. van Boom; R. M. J. Liskamp

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 235 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901090106

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✦ Synopsis

Abstract

N, N‐diisopropyl‐bis(4‐chlorobenzyl) phosphoramidite is an easily accessible phosphitylating agent, which readily phosphorylates Boc‐Ser‐OMe, Boc‐Thr‐OMe and Boc‐Tyr‐OMe in good to high yields after t‐BuOOH or MCPBA oxidation. The Boc‐group can be removed without affecting the phosphate 4‐chlorobenzyl groups and vice versa. Extension of the Boc‐deprotected phosphoamino acids with a subsequent amino acid yields the corresponding protected phosphopeptides

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