Effect of histidine methylation on the recognition of OVA323-336 T-epitope: Synthesis of N-α-Fmoc-N-τ-methyl-L-histidine and its use for the synthesis of two histidine methylated analogues of OVA323-336 |
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Authors: | Stéphane Eifler Isabelle Leblond Elisabeth Trifilieff Jean-Pierre Lepoittevin |
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Institution: | (1) Laboratoire de Dermatochimie associé au CNRS, Université Louis Pasteur, Clinique Dermatologique, CHU, F-67091 Strasbourg Cedex, France;(2) Laboratoire de Chimie Organique des Substances Naturelles associé au CNRS, Université Louis Pasteur, Centre de Neurochimie, 5, rue Blaise Pascal, F-67084 Strasbourg Cedex, France |
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Abstract: | Summary N-α-Fmoc-N-τ-methyl-L-histidine was prepared in three steps fromN-α-Boc-L-histidine by treatment with methyliodine in DMF at−10°C, deprotection of theN-α position in pure TFA and subsequent reprotection by Fmoc-chloroformate in a 5% Na2CO3/dioxane mixture.N-α-Fmoc-N-τ-methyl-L-histidine was then used for the solid-phase synthesis of two analogues of the OVA323–336 T-epitope, methylated on His331 and on His328/331, respectively. These peptides were tested for their ability to activate 3 DO-54.8 T-cell hybridoma when presented by fixed
A-20.1.11 antigen presenting cells, and no significant difference was observed in IL-2 production. |
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Keywords: | Allergic contact dermatitis Antigenic peptide Fmoc chemistry Solid-phase synthesis Synthetic peptide |
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