Document Detail

Development of a hypersensitive periodate-cleavable amino acid that is methionine- and disulfide-compatible and its application in MHC exchange reagents for T cell characterisation.
MedLine Citation:
PMID:  23280887     Owner:  NLM     Status:  MEDLINE    
Incorporation of cleavable linkers into peptides and proteins is of particular value in the study of biological processes. Here we describe the synthesis of a cleavable linker that is hypersensitive to oxidative cleavage as the result of the periodate reactivity of a vicinal amino alcohol moiety. Two strategies directed towards the synthesis of a building block suitable for solid-phase peptide synthesis were developed: a chemoenzymatic route, involving L-threonine aldolase, and an enantioselective chemical route; these led to α,γ-diamino-β-hydroxybutanoic acids in diastereoisomerically mixed and enantiopure forms, respectively. Incorporation of the 1,2-amino alcohol linker into the backbone of a peptide generated a conditional peptide that was rapidly cleaved at very low concentrations of sodium periodate. This cleavable peptide ligand was applied in the generation of MHC exchange reagents for the detection of antigen-specific T cells in peripheral blood cells. The extremely low concentration of periodate required to trigger MHC peptide exchange allowed the co-oxidation of methionine and disulfide residues to be avoided. Conditional MHC reagents hypersensitive to periodate can now be applied without limitations when UV irradiation is undesired or less practical.
Alessia Amore; Kim Wals; Evelyn Koekoek; Rieuwert Hoppes; Mireille Toebes; Ton N M Schumacher; Boris Rodenko; Huib Ovaa
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chembiochem : a European journal of chemical biology     Volume:  14     ISSN:  1439-7633     ISO Abbreviation:  Chembiochem     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-01-02     Completed Date:  2013-06-10     Revised Date:  2013-07-11    
Medline Journal Info:
Nlm Unique ID:  100937360     Medline TA:  Chembiochem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  123-31     Citation Subset:  IM    
Copyright Information:
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Division of Cell Biology, The Netherlands Cancer Institute, Plesmanlaan 121, 1066 CX Amsterdam, the Netherlands.
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MeSH Terms
Amino Acid Sequence
Amino Acids / chemical synthesis,  chemistry*,  metabolism,  pharmacology*
Amino Alcohols / chemistry
Biocompatible Materials / chemical synthesis,  chemistry,  metabolism,  pharmacology
Disulfides / chemistry*
Drug Discovery
HLA-A2 Antigen / chemistry*,  metabolism*
Indicators and Reagents / chemistry
Periodic Acid / pharmacology*
Substrate Specificity
T-Lymphocytes / drug effects,  metabolism*
Reg. No./Substance:
0/Amino Acids; 0/Amino Alcohols; 0/Biocompatible Materials; 0/Disulfides; 0/HLA-A2 Antigen; 0/Indicators and Reagents; 10450-60-9/Periodic Acid; 63-68-3/Methionine

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