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https://hdl.handle.net/2440/92451
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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 1521-3765 |
Statement of Responsibility: | 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 |
Grant ID: | http://purl.org/au-research/grants/nhmrc/1023321 http://purl.org/au-research/grants/nhmrc/1023078 |
Published version: | http://dx.doi.org/10.1002/chem.201403574 |
Appears in Collections: | Aurora harvest 2 IPAS publications |
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