2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin

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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.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.identifier.citationChemistry: A European Journal, 2014; 20(31):9549-9552
dc.identifier.doi10.1002/chem.201403574
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttp://hdl.handle.net/2440/92451
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.relation.granthttp://purl.org/au-research/grants/nhmrc/1023321
dc.relation.granthttp://purl.org/au-research/grants/nhmrc/1023078
dc.rights© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.source.urihttps://doi.org/10.1002/chem.201403574
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
pubs.publication-statusPublished

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