Convenient synthesis of acetonide-protected 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis

TETRAHEDRON LETTERS

卷:49

Article

Liu, Zhongqiang¹  Hu, Bi-Huang¹  Messersmith, Phillip B.¹ 

[1] Northwestern Univ, Dept Biomed Engn, Evanston, IL 60208 USA

关键词: DOPA;    Fmoc-DOPA(acetonide)-OH;    acetonide;   

DOI  :  10.1016/j.tetlet.2008.07.052

来源: Elsevier

【 摘 要 】

We report a facile approach to the synthesis of acetonide and Fmoc-protected 3,4-dihydroxyphenylalanine (DOPA), Fmoc-DOPA(acetonide)-OH. By protecting the amino group of DOPA with a phthaloyl group and the carboxyl group as a methyl ester, acetonide protection of the catechol of DOPA derivative was realized in the presence of p-toluenesulfonic acid. Following removal of protecting groups, the intermediate was converted to Fmoc-DOPA(acetonide)-OH, which was successfully incorporated into a short DOPA-containing peptide, derived from marine tubeworm cement proteins Pc1 and Pc2. (C) 2008 Elsevier Ltd. All rights reserved.

【 授权许可】

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