ArticleTetrahedron letters2008
Convenient Synthesis of Acetonide Protected 3,4-Dihydroxyphenylalanine (DOPA) for Fmoc Solid-Phase Peptide Synthesis.
Article in Tetrahedron letters, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 28 citations in OpenAlex.
- First Synthesis of Shimobashiric Acid C With Acetonide as the Catechol Protecting Group.Chemistry & biodiversity · 2026Article
- Development of a KRP-based pH-responsive drug delivery system for solid tumors.Translational cancer research · 2025Article
- Harnessing Nature-Inspired Catechol Amino Acid to Engineer Sticky Proteins and Bacteria.Small methods · 2024Article
- Rheology and Gelation of Hyaluronic Acid/Chitosan Coacervates.Biomolecules · 2022Article
- Mussel-inspired biomaterials: From chemistry to clinic.Bioengineering & translational medicine · 2022Review
- Article
- Recent approaches in designing bioadhesive materials inspired by mussel adhesive protein.Journal of polymer science. Part A, Polymer chemistry · 2017Review
- 3,4-Dihydroxyphenylalanine Peptides as Nonperturbative Quantum Dot Sensors of Aminopeptidase.ACS nano · 2016Article
- Acetonide Protection of Dopamine for the Synthesis of Highly Pure N-docosahexaenoyldopamine.Tetrahedron letters · 2010Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
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.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.