Role of arginine in chemical cross-linking with N-hydroxysuccinimide esters |
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Authors: | Stefanie Mädler |
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Institution: | Department of Chemistry and Applied Biosciences, ETH Zurich, CH-8093 Zurich, Switzerland |
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Abstract: | In order to clarify whether arginine has a promoting effect on the acylation of hydroxyl groups of serine, threonine, or tyrosine by homobifunctional cross-linking agents in aqueous solution, we carried out systematic experiments with model peptides, comparing relative reaction yields with covalently protected and unprotected arginines by MALDI-MS. The guanidinium group could be demonstrated to contribute to the reactivity of hydroxyl groups toward N-hydroxysuccinimide esters and catalyze the nucleophilic substitution, probably via hydrogen bonds. |
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