Haptenization of ovalbumin with the skin sensitizer methyl octanesulfonate: Characterization of the methylated OVA323-339 T-cell epitope at His331

被引:6
作者
Henriot, S
Lepoittevin, JP
Trifilieff, E
机构
[1] Univ Strasbourg 1, Lab Chim Organ Subst Nat, UMR 7509, CNRS, F-67084 Strasbourg, France
[2] CHU Strasbourg, Lab Dermatochim, UMR 7509, CNRS,ULP,Clin Dermatol, F-67000 Strasbourg, France
关键词
allergic contact dermatitis; methyl octanesulfonate; methylated histidine; OVA323-339; ovalbumin; solid phase peptide synthesis; T-cell epitope;
D O I
10.1002/psc.328
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Our interest is focused on the induction of allergic contact dermatitis (ACD) by the strong skin sensitizer, methyl octanesulfonate, which is a potent methyl transfer agent, especially to histidine and methionine residues. We are particularly interested to study the effect of methylation on the presentation and recognition of the ovalbumin (OVA) T-cell epitope. OVA323-339, by the T-cell receptor (TCR). Here we report the synthesis of the modified monomer N-alpha -Fmoc-N-tau -methyl-L-histidine and its incorporation by solid phase synthesis into the three possible methylated analogues of OVA323-339, that were needed as references for the subsequent studies. Native OVA was haptenized by methyl octanesulfonate. Using classical protein chemistry techniques (trypsin digestion, gel permeation, HPLC, MS and Edman sequencing) we were able to show that OVA323-339 was selectively methylated at His331. Circular dichroism (CD) studies showed that the methylation has no influence on the secondary structure of the peptide. Copyright (C) 2001 European Peptide Society and John Wiley & Sons. Ltd,
引用
收藏
页码:331 / 337
页数:7
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