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2‐Nitroveratryl as a Photocleavable Thiol‐Protecting Group for Directed Disulfide Bond Formation in the Chemical Synthesis of Insulin |
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| Authors: | John A Karas Dr Denis B Scanlon Prof Briony E Forbes Dr Irina Vetter Prof Richard J Lewis Dr James Gardiner Prof Frances Separovic Prof John D Wade Dr Mohammed A Hossain |
| Institution: | 1. The Florey Institute of Neuroscience and Mental Health, The University of Melbourne, 30 Royal Parade, Parkville, Victoria 3052 (Australia);2. School of Chemistry, The University of Melbourne, Victoria 3010 (Australia);3. Materials Science and Engineering, CSIRO, Clayton, Victoria 3168 (Australia);4. Department of Chemistry, The University of Adelaide, South Australia 5005 (Australia);5. Medical Biochemistry, Flinders University, Sturt Road, Bedford Park 5042, South Australia (Australia);6. Institute for Molecular Bioscience, The University of Queensland, St. Lucia 4072, Queensland (Australia) |
| 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 |