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Evaluation of strategies for ‘one-pot’ deprotection, cleavage and disulfide bond formation in the preparation of cystine-containing peptides

✍ Scribed by Jane C. Spetzler; Morten Meldal

Publisher: Springer Netherlands
Year: 1997
Tongue: English
Weight: 329 KB
Volume: 3
Category: Article
ISSN: 1573-3149
DOI: 10.1007/bf00127963

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✦ Synopsis

Oxytocin, a nonapeptide amide, was synthesized on a PEGA-resin using the Fmoc-tBu strategy. The sulfhydryl groups of the two cysteine residues were protected with trityl groups. Different oxidation reagents such as DMSO, 12 and thallium(III) trifluoroacetate mixed with TFA were evaluated in order to obtain oxytocin in a one-pot reaction. The mixture of TFA and DMSO (5:1) in which oxytocin was formed quantitatively was found to be the optimal method. The cyclic oxytocin could be isolated in 56% yield.

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