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Type: Journal article
Title: 2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin
Author: Karas, J.
Scanlon, D.
Forbes, B.
Vetter, I.
Lewis, R.
Gardiner, J.
Separovic, F.
Wade, J.
Hossain, M.
Citation: Chemistry: A European Journal, 2014; 20(31):9549-9552
Publisher: Wiley-VCH Verlag
Issue Date: 2014
ISSN: 0947-6539
Statement of
John A. Karas, Denis B. Scanlon, Briony E. Forbes, Irina Vetter, Richard J. Lewis, James Gardiner, Frances Separovic, John D. Wade and Mohammed A. Hossain
Abstract: Chemical 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.
Keywords: cysteine-protecting groups; insulin; peptides; photochemistry; regioselectivity
Rights: © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
DOI: 10.1002/chem.201403574
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