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Solid-phase synthesis of peptides using allylic anchoring groups 2. Palladium-catalysed cleavage of Fmoc-protected peptides

✍ Scribed by Paul Lloyd-Williams; Ahmed Merzouk; François Guibé; Fernando Albericio; Ernest Giralt

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
384 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

High yklds for the cleavage reaction of Fmoc-protected peptide segments fmn an allylic handle may be obtained using tributyltin hydride in the jmsence of (ph3P)PdQ in a 1:l mixture of DMF/DCM. Altematively tbe cleavage reacdon may be carried out using NMA as nuclecpbile in a 2:2:1 mixture of DMSOfl'HF/O.SM HCI in the presence of (Ph3P)qW. The Fmoc group is completely stable to both t&e cleavage methods.

The solid-phase synthesis of peptides using ally1 handles was first reported by Kunz.3 The use of such anchoring groups for the synthesis of protected peptide segments4 is attractive because, in principle, they are compatible with both the Boc/Bzl-and Fmoc/rBu-peptide synthesis strategies. Moreover for the FmocJrBu strategy the allylic anchor provides a three-dimensional orthogonol5~ 6 protecting scheme.

Peptides may be cleaved from this type of solid support by an ally1 transfer reaction brought about by treatment of a suspension of the the peptide-resin in a suitable solvent with a nucleophile (which acts an ally1

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