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Lookup NU author(s): Duncan MillerORCiD, Dr Benoit Carbain, Dr Gary Beale, Dr Sari Alhasan, Professor Helen ReevesORCiD, Dr Ulrich Baisch, Professor Herbie Newell, Emeritus Professor Bernard Golding, Professor Roger Griffin
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0).
Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S, 3R, 4R, 5S, 6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl) tetrahydro-2H-pyran-3-yl) sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.
Author(s): Miller DC, Carbain B, Beale GS, Alhasan SF, Reeves HL, Baisch U, Newell DR, Golding BT, Griffin RJ
Publication type: Article
Publication status: Published
Journal: Organic & Biomolecular Chemistry
Year: 2015
Volume: 13
Issue: 18
Pages: 5279-5284
Print publication date: 14/05/2015
Online publication date: 31/03/2015
Acceptance date: 31/03/2015
Date deposited: 15/12/2015
ISSN (print): 1477-0520
ISSN (electronic): 1477-0539
Publisher: Royal Society of Chemistry
URL: http://dx.doi.org/10.1039/c5ob00211g
DOI: 10.1039/c5ob00211g
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