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|Title:||2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin|
|Citation:||Chemistry: A European Journal, 2014; 20(31):9549-9552|
|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|
|Appears in Collections:||Aurora harvest 2|
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