title: 2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin.
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.
authors: The Florey Institute of Neuroscience and Mental Health, The University of Melbourne, 30 Royal Parade, Parkville, Victoria 3052 (Australia); School of Chemistry, The University of Melbourne, Victoria 3010 (Australia); Materials Science and Engineering, CSIRO, Clayton, Victoria 3168 (Australia).
authors: John A
authors: JA
authors: Karas
authors: Denis B
authors: DB
authors: Scanlon
authors: Briony E
authors: BE
authors: Forbes
authors: Irina
authors: I
authors: Vetter
authors: Richard J
authors: RJ
authors: Lewis
authors: James
authors: J
authors: Gardiner
authors: Frances
authors: F
authors: Separovic
authors: John D
authors: JD
authors: Wade
authors: Mohammed A
authors: MA
authors: Hossain
mesh_terms: D003545:Cysteine / Q000737:chemistry; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry; D007328:Insulin / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D004220:Disulfides; D007328:Insulin; D009574:Nitro Compounds; D010455:Peptides; D013438:Sulfhydryl Compounds; D003545:Cysteine
keywords: cysteine-protecting groups; insulin; peptides; photochemistry; regioselectivity