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2‐Nitroveratryl as a Photocleavable Thiol‐Protecting Group for Directed Disulfide Bond Formation in the Chemical Synthesis of Insulin
Author(s) -
Karas John A.,
Scanlon Denis B.,
Forbes Briony E.,
Vetter Irina,
Lewis Richard J.,
Gardiner James,
Separovic Frances,
Wade John D.,
Hossain Mohammed A.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403574
Subject(s) - thiol , chemistry , disulfide bond , regioselectivity , cystine , protecting group , combinatorial chemistry , group (periodic table) , solid phase synthesis , cysteine , human insulin , insulin , organic chemistry , peptide , biochemistry , catalysis , enzyme , medicine , alkyl , endocrinology
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.