1.Convenient Synthesis of Acetonide Protected 3,4-Dihydroxyphenylalanine (DOPA) for Fmoc Solid-Phase Peptide Synthesis.
Liu Z1, Hu BH, Messersmith PB. Tetrahedron Lett. 2008 Sep 15;49(38):5519-5521.
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.