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Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

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.

Publication metadata

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


DOI: 10.1039/c5ob00211g


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