A highly efficient method for the preparation of phosphinic pseudodipeptidic blocks suitably protected for solid-phase peptide synthesis

Building blocks of the general type FmocXaa Psi {PO(OAd)CH2} YaaOH suitable for solid-phase synthesis of phosphinic peptides have been prepared using a new synthetic strategy based on mild and high-yielding reactions. The key reaction of this method is the Michael addition of activated Fmoc protecte...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 16; pp. 3471 - 3478
Main Authors Georgiadis, D, Matziari, M, Yiotakis, A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 16.04.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
zinc metalloprotease inhibitors
POTENT
phosphinic peptides
INHIBITORS
ACIDS
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Summary:Building blocks of the general type FmocXaa Psi {PO(OAd)CH2} YaaOH suitable for solid-phase synthesis of phosphinic peptides have been prepared using a new synthetic strategy based on mild and high-yielding reactions. The key reaction of this method is the Michael addition of activated Fmoc protected silyl aminophosphonites to benzyl acrylates at room temperature. As compared to our previous work, this method consists of less synthetic steps and doubles the overall yield, thus providing a convenient route to phosphinic synthons suitable for the solid-phase preparation of inhibitors of various metalloproteases. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)00221-6