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Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis

✍ Scribed by Bi-Huang Hu; Phillip B Messersmith

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
110 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cyclic ethyl orthoformate (Ceof) was utilized as a protecting group to protect the catechol hydroxyl groups of 3,4-dihydroxyphenylalanine (DOPA). This protecting group is stable to strong bases and nucleophiles, and can be removed eciently by 1 M trimethylsilyl bromide in triΒ―uoroacetic acid in the presence of scavengers at 0 C for 60 min. Fmoc-DOPA(Ceof)-OH was synthesized in high yield and applied along with other Fmoc-amino acids to the solid-phase peptide synthesis of a DOPA-containing decapeptide from a mussel adhesive protein.

πŸ“œ SIMILAR VOLUMES

Solid-phase synthesis of peptides using
Solid-phase synthesis of peptides using allylic anchoring groups 2. Palladium-catalysed cleavage of Fmoc-protected peptides
✍ Paul Lloyd-Williams; Ahmed Merzouk; FranΓ§ois GuibΓ©; Fernando Albericio; Ernest G πŸ“‚ Article πŸ“… 1994 πŸ› Elsevier Science 🌐 French βš– 384 KB

High yklds for the cleavage reaction of Fmoc-protected peptide segments fmn an allylic handle may be obtained using tributyltin hydride in the jmsence of (ph3P)PdQ in a 1:l mixture of DMF/DCM. Altematively tbe cleavage reacdon may be carried out using NMA as nuclecpbile in a 2:2:1 mixture of DMSOfl'