Site‐specific labeling of synthetic peptide using the chemoselective reaction between N‐methoxyamino acid and isothiocyanate |
| |
Authors: | Toshiaki Hara Euis Maras Purwati Akira Tainosyo Toru Kawakami Hironobu Hojo Saburo Aimoto |
| |
Institution: | 1. Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka, Japan;2. Institute for Protein Research, Osaka University, Suita, Osaka, Japan |
| |
Abstract: | 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 Lys10 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. |
| |
Keywords: | site‐specific labeling N‐methoxyamino acid isothiocyanate human β ‐defensin |
|
|