Abstract |
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.
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Authors | S Henriot, J P Lepoitrevin, E Trifilieff |
Journal | Journal of peptide science : an official publication of the European Peptide Society
(J Pept Sci)
Vol. 7
Issue 6
Pg. 331-7
(Jun 2001)
ISSN: 1075-2617 [Print] England |
PMID | 11461047
(Publication Type: Journal Article)
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Chemical References |
- Alkanesulfonates
- Allergens
- Epitopes, T-Lymphocyte
- Haptens
- Irritants
- methyl octanesulfonate
- Histidine
- Ovalbumin
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Topics |
- Alkanesulfonates
(chemistry, immunology)
- Allergens
(chemistry, immunology)
- Animals
- Chickens
- Chromatography, Gel
- Chromatography, High Pressure Liquid
- Circular Dichroism
- Epitopes, T-Lymphocyte
(chemistry)
- Haptens
(chemistry, immunology)
- Histidine
(analogs & derivatives, chemical synthesis, chemistry)
- Irritants
(chemistry, immunology)
- Methylation
- Ovalbumin
(chemistry, immunology)
- Protein Structure, Secondary
- Structure-Activity Relationship
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