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A method for the one-pot regioselective formation of the two disulfide bonds of α-conotoxin SI

✍ Scribed by Alan Cuthbertson; Bård Indrevoll

Book ID
104210240
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
78 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A one-pot method for the regioselective formation of the disulfide bridges of α-conotoxin SI employing temperature-controlled orthogonal protecting groups is reported. The pairing of t-butyl and 4-methylbenzyl sidechain protecting groups was chosen for the four cysteine residues. Cleavage of the peptide from a solid support afforded a fully S-protected crude product. The first disulfide bridge was formed directly from the crude material by simultaneous cleavage and oxidation of the t-butyl groups in TFA:DMSO:anisole (97.9:2:0.1) at room temperature. The subsequent heating of this solution resulted in the cleavage of the 4-methylbenzyl groups with simultaneous oxidation yielding the desired bicyclic product.

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