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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.

SUBMITTER: Liu Z

PROVIDER: S-EPMC2598405 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

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

Liu Zhongqiang Z Hu Bi-Huang BH Messersmith Phillip B PB

Tetrahedron letters 20080901 38

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 ...[more]

PMID: 19759805

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Reactions of DOPA (3,4-dihydroxyphenylalanine) decarboxylase with DOPA.

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Silk/Natural Rubber (NR) and 3,4-Dihydroxyphenylalanine (DOPA)-Modified Silk/NR Composites: Synthesis, Secondary Structure, and Mechanical Properties.

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