USE OF ALLOC-AMINO ACIDS IN SOLID-PHASE PEPTIDE-SYNTHESIS - TANDEM DEPROTECTION-COUPLING REACTIONS USING NEUTRAL CONDITIONS

Authors
THIERIET N ALSINA J GIRALT E GUIBE F ALBERICIO F
Citation
N. Thieriet et al., USE OF ALLOC-AMINO ACIDS IN SOLID-PHASE PEPTIDE-SYNTHESIS - TANDEM DEPROTECTION-COUPLING REACTIONS USING NEUTRAL CONDITIONS, Tetrahedron letters, 38(41), 1997, pp. 7275-7278
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
41
Year of publication
1997
Pages
7275 - 7278
Database
ISI
SICI code
0040-4039(1997)38:41<7275:UOAAIS>2.0.ZU;2-O
Abstract
The use of Alloc group in SPPS for the N-alpha protection of amino aci ds is an alternative to the Boc and Fmoc protecting groups. The smooth removal of Alloc group in neutral conditions with catalytic amounts o f Pd(PPh3)(4) in the presence of PhSiH3 as a scavenger for the allyl s ystem permits orthogonality with the most common protecting groups. Fu rthermore, a tandem deprotection-coupling reaction allows the suppress ion of DKP formation in cases where this side reaction is troublesome. (C) 1997 Elsevier Science Ltd.