Preparation of Deuterated Methyl and Dimethyl Substituted Nicotinoylating Agents for Derivatization of the N-Terminal of Protein

Hiroki Tsumoto; Chie Murata; Naoki Miyata; Ryo Taguchi; Kohfuku Kohda

doi:10.1248/cpb.51.1399

Regular Articles

Preparation of Deuterated Methyl and Dimethyl Substituted Nicotinoylating Agents for Derivatization of the N-Terminal of Protein

Hiroki Tsumoto, Chie Murata, Naoki Miyata, Ryo Taguchi, Kohfuku Kohda

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Keywords: nicotinoylating agent, N-terminal, protein, mass spectrometry, D-label, differential expression analysis

JOURNAL FREE ACCESS

2003 Volume 51 Issue 12 Pages 1399-1401

DOI https://doi.org/10.1248/cpb.51.1399

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Abstract

Methyl groups of 6-methylnicotinic acid and 2,6-dimethylnicotinic acid were deuterated by an H–D exchange reaction under conditions of 1% NaOD/D₂O on heating. With a condensation reaction between the D-labeled nicotinic acid derivative and N-hydroxysuccinimide with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, the nicotinoylating agents, 1-(6-methyl[D₃]nicotinoyloxy)succinimide (2c) and 1-(2,6-dimethyl[D₆]nicotinoyloxy)succinimide (2f) were prepared. Both D-labeled nicotinoylating agents and their unlabeled counterparts quantitatively modified the N-terminal of protein.

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