Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 31, Pages 9549-9552Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403574
Keywords
cysteine-protecting groups; insulin; peptides; photochemistry; regioselectivity
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Funding
- NHMRC [1023321, 1023078]
- C.S.I.R.O. (Australia)
- Victorian Government Operational Infrastructure Support Program
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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.
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