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Site‐specific labeling of synthetic peptide using the chemoselective reaction between N ‐methoxyamino acid and isothiocyanate
Author(s) -
Hara Toshiaki,
Purwati Euis Maras,
Tainosyo Akira,
Kawakami Toru,
Hojo Hironobu,
Aimoto Saburo
Publication year - 2015
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2803
Subject(s) - isothiocyanate , chemistry , peptide , combinatorial chemistry , biochemistry
Site‐specific labeling of synthetic peptides carrying N ‐methoxyglycine (MeOGly) by isothiocyanate is demonstrated. A nonapeptide having MeOGly at its N ‐terminus was synthesized by the solid‐phase method and reacted with phenylisothiocyanate under various conditions. In acidic solution, the reaction specifically gave a peptide having phenylthiourea structure at its N ‐terminus, leaving side chain amino group intact. The synthetic human β ‐defensin‐2 carrying MeOGly at its N ‐terminus or the side chain amino group of Lys 10 reacted with phenylisothiocyanate or fluorescein isothiocyanate also at the N ‐methoxyamino group under the same conditions, demonstrating that this method is generally useful for the site‐specific labeling of linear synthetic peptides as well as disulfide‐containing peptides. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.