Journal
TETRAHEDRON LETTERS
Volume 49, Issue 38, Pages 5519-5521Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.07.052
Keywords
DOPA; Fmoc-DOPA(acetonide)-OH; acetonide
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Funding
- NIDCR NIH HHS [R01 DE014193, R37 DE014193, R01 DE014193-04] Funding Source: Medline
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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.
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