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

Details

Serval ID
serval:BIB_8301
Type
Article: article from journal or magazin.
Collection
Publications
Title
Chemoselectively addressable HCan building blocks in peptide synthesis: L-homocanaline derivatives.
Journal
Journal of Peptide Science : An Official Publication of the European Peptide Society
Author(s)
Lang I., Donzé N., Garrouste P., Dumy P., Mutter M.
ISSN
1075-2617 (Print)
ISSN-L
1075-2617
Publication state
Published
Issued date
1998
Volume
4
Number
1
Pages
72-80
Language
english
Notes
Publication types: Journal Article ; Research Support, Non-U.S. Gov't
Publication Status: ppublish
Abstract
(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.
Keywords
Aminobutyrates/chemistry, Chromatography, High Pressure Liquid, Chromatography, Thin Layer, Magnetic Resonance Spectroscopy, Peptides/chemical synthesis
Pubmed
Create date
19/11/2007 11:37
Last modification date
03/03/2018 18:51
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