Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/92451
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dc.contributor.authorKaras, J.-
dc.contributor.authorScanlon, D.-
dc.contributor.authorForbes, B.-
dc.contributor.authorVetter, I.-
dc.contributor.authorLewis, R.-
dc.contributor.authorGardiner, J.-
dc.contributor.authorSeparovic, F.-
dc.contributor.authorWade, J.-
dc.contributor.authorHossain, M.-
dc.date.issued2014-
dc.identifier.citationChemistry: A European Journal, 2014; 20(31):9549-9552-
dc.identifier.issn0947-6539-
dc.identifier.issn1521-3765-
dc.identifier.urihttp://hdl.handle.net/2440/92451-
dc.description.abstractChemical synthesis of peptides can allow the option of sequential formation of multiple cysteines through exploitation of judiciously chosen regioselective thiol-protecting groups. We report the use of 2-nitroveratryl (oNv) as a new orthogonal group that can be cleaved by photolysis under ambient conditions. In combination with complementary S-pyridinesulfenyl activation, disulfide bonds are formed rapidly in situ. The preparation of Fmoc-Cys(oNv)-OH is described together with its use for the solid-phase synthesis of complex cystine-rich peptides, such as insulin.-
dc.description.statementofresponsibilityJohn A. Karas, Denis B. Scanlon, Briony E. Forbes, Irina Vetter, Richard J. Lewis, James Gardiner, Frances Separovic, John D. Wade and Mohammed A. Hossain-
dc.language.isoen-
dc.publisherWiley-VCH Verlag-
dc.rights© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim-
dc.subjectcysteine-protecting groups; insulin; peptides; photochemistry; regioselectivity-
dc.title2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin-
dc.typeJournal article-
dc.identifier.doi10.1002/chem.201403574-
dc.relation.granthttp://purl.org/au-research/grants/nhmrc/1023321-
dc.relation.granthttp://purl.org/au-research/grants/nhmrc/1023078-
pubs.publication-statusPublished-
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