Chemoselectively addressable HCan building blocks in peptide synthesis: L-homocanaline derivatives.

Détails

ID Serval
serval:BIB_8301
Type
Article: article d'un périodique ou d'un magazine.
Collection
Publications
Titre
Chemoselectively addressable HCan building blocks in peptide synthesis: L-homocanaline derivatives.
Périodique
Journal of Peptide Science : An Official Publication of the European Peptide Society
Auteur(s)
Lang I., Donzé N., Garrouste P., Dumy P., Mutter M.
ISSN
1075-2617 (Print)
ISSN-L
1075-2617
Statut éditorial
Publié
Date de publication
1998
Volume
4
Numéro
1
Pages
72-80
Langue
anglais
Notes
Publication types: Journal Article ; Research Support, Non-U.S. Gov't
Publication Status: ppublish
Résumé
(S-2-amino-5-(aminooxy)pentanoic acid (L-homocanaline, HCan), a structural analogue of lysine, contains a reactive alkyloxyamine side chain and is therefore considered to react chemoselectively with carbonyl compounds by forming a kinetically stable oxime bond. The chemical synthesis of L-homocanaline starting from protected glutamic acid derivatives is described. Two orthogonally protected homocanaline derivatives were synthesized and their use in standard SPPS procedures was exemplified for the synthesis of a chemoselectively addressable cyclic peptide for use in TASP design. Moreover, the wide range of applications of this unique building block was demonstrated for the chemoselective ligation of an unprotected disaccharide to a HCan containing model peptide resulting in a chimeric glycopeptide structure.
Mots-clé
Aminobutyrates/chemistry, Chromatography, High Pressure Liquid, Chromatography, Thin Layer, Magnetic Resonance Spectroscopy, Peptides/chemical synthesis
Pubmed
Création de la notice
19/11/2007 11:37
Dernière modification de la notice
20/08/2019 15:42
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