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Elsevier, Tetrahedron Letters, 38(49), p. 5519-5521

DOI: 10.1016/j.tetlet.2008.07.052

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Convenient Synthesis of Acetonide Protected 3,4-Dihydroxyphenylalanine (DOPA) for Fmoc Solid-Phase Peptide Synthesis

Journal article published in 2008 by Zhongqiang Liu, Bi-Huang Hu, Phillip B. Messersmith ORCID
This paper is available in a repository.
This paper is available in a repository.

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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.