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Title

Synthesis of cyclic peptides from unprotected precursors using removable N alpha-(1-(4-methoxyphenyl)-2-mercaptoethyl) auxiliary

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Published in Journal of Peptide Research. 2003, vol. 61, no. 3, p. 152-7
Abstract A new method to cyclize unprotected peptides is presented. The method involves the use of a 1-phenyl-2-mercaptoethyl derivative on the N-terminal glycine. This template acts as an auxiliary thiol-containing group in order to drive cyclization with a counterpart thioester moiety on the same molecule. Subsequent facile removal of the derivative generates products with only native peptide structure. The successful, high-yield cyclization of the peptide GSPYSSDTTPA is described.
Keywords ChromatographyHigh Pressure LiquidDimethylformamide/chemistryEsters/chemistryGlycine/chemistryHydrogen-Ion ConcentrationMethylene Chloride/chemistryModelsChemicalPeptide BiosynthesisPeptides/chemistryProtein StructureTertiaryResinsSyntheticTime FactorsTrifluoroacetic Acid/chemistry
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PMID: 12558950
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Research group HIV (835)
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CARDONA, Valérie, HARTLEY, Oliver, BOTTI, Paolo. Synthesis of cyclic peptides from unprotected precursors using removable N alpha-(1-(4-methoxyphenyl)-2-mercaptoethyl) auxiliary. In: Journal of Peptide Research, 2003, vol. 61, n° 3, p. 152-7. https://archive-ouverte.unige.ch/unige:26076

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Deposited on : 2013-01-31

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