2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin.

Karas, John A., Scanlon, Denis B., Forbes, Briony E., Vetter, Irina, Lewis, Richard J., Gardiner, James, Separovic, Frances, Wade, John D. and Hossain, Mohammed A. (2014) 2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin.. Chemistry: A European Journal, 20 31: 9549-9552. doi:10.1002/chem.201403574


Author Karas, John A.
Scanlon, Denis B.
Forbes, Briony E.
Vetter, Irina
Lewis, Richard J.
Gardiner, James
Separovic, Frances
Wade, John D.
Hossain, Mohammed A.
Title 2-nitroveratryl as a photocleavable thiol-protecting group for directed disulfide bond formation in the chemical synthesis of insulin.
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 1521-3765
0947-6539
Publication date 2014-07-28
Year available 2014
Sub-type Article (original research)
DOI 10.1002/chem.201403574
Open Access Status
Volume 20
Issue 31
Start page 9549
End page 9552
Total pages 4
Place of publication Weinheim, Germany
Publisher Wiley
Collection year 2015
Language eng
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.
Keyword Cysteine-protecting groups
Insulin
Peptides
Photochemistry
Regioselectivity
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2015 Collection
Institute for Molecular Bioscience - Publications
 
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Created: Tue, 05 Aug 2014, 12:45:44 EST by Dr Irina Vetter on behalf of Institute for Molecular Bioscience