Document Detail

A novel heterotrifunctional peptide-based cross-linking reagent for facile access to bioconjugates. Applications to peptide fluorescent labelling and immobilisation.
MedLine Citation:
PMID:  18698464     Owner:  NLM     Status:  MEDLINE    
A convenient, versatile and straightforward synthesis of a novel heterotrifunctional peptide-based linker molecule is described. This generic bio-labelling reagent contains an amine-reactive N-hydroxysuccinimidyl carbamate moiety, an aldehyde/ketone-reactive aminooxy group and a thiol group with a propensity to form urea, oxime and thioether linkages respectively. The full chemical orthogonality between the free aminooxy and thiol functionalities was demonstrated through the preparation of a fluorescent reagent suitable for the selective staining of a carboxaldehyde-modified surface by means of oxime ligation. The absence of reactivity of these two functions toward the nucleophile-sensitive active carbamate was obtained by using temporary aminooxy- and thiol-protecting groups removable under mild conditions. The utility of the linker molecule to cross-link three different molecular partners has been illustrated by the preparation of fluorescent tripod-functionalised surfaces which may be useful in developing new peptide microarrays and related immunosensors.
Guillaume Clav?; Herv? Boutal; Antoine Hoang; Fran?ois Perraut; Herv? Volland; Pierre-Yves Renard; Anthony Romieu
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-06-30
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  6     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-08-13     Completed Date:  2008-11-17     Revised Date:  2010-03-29    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  3065-78     Citation Subset:  IM    
Equipe de Chimie Bio-Organique, COBRA - CNRS UMR 6014, rue Lucien Tesni?re, 76131, Mont-Saint-Aignan, France.
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MeSH Terms
Chromatography, High Pressure Liquid
Cross-Linking Reagents / chemical synthesis*,  chemistry
Fluorescence Resonance Energy Transfer
Fluorescent Dyes / chemistry*
Fluoroimmunoassay / methods*
Substance P / chemistry*,  immunology,  metabolism*
Sulfhydryl Compounds / chemistry
Reg. No./Substance:
0/Cross-Linking Reagents; 0/Fluorescent Dyes; 0/Sulfhydryl Compounds; 33507-63-0/Substance P
Erratum In:
Org Biomol Chem. 2009 Dec 21;7(24):5271

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