title: Convenient Synthesis of Acetonide Protected 3,4-Dihydroxyphenylalanine (DOPA) for Fmoc Solid-Phase Peptide Synthesis.
abstract: 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.
authors.affiliation: Department of Biomedical Engineering, Northwestern University, Evanston 60208, US.
authors.forename: Zhongqiang
authors.initials: Z
authors.lastname: Liu
authors.forename: Bi-Huang
authors.initials: BH
authors.lastname: Hu
authors.forename: Phillip B
authors.initials: PB
authors.lastname: Messersmith