Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

Benjamin Ayers; Hilary Long; Edith Sim; Iain A Smellie; Brendan Wilkinson; Antony J Fairbanks

doi:10.1016/j.carres.2009.02.006

Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

Benjamin Ayers
, Hilary Long
, Edith Sim
, Iain A Smellie
, Brendan Wilkinson
, Antony J Fairbanks

Chemistry

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

A series of β-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain.

Original language	English
Pages (from-to)	739-746
Journal	Carbohydrate Research
Volume	344
Issue number	6
DOIs	https://doi.org/10.1016/j.carres.2009.02.006
Publication status	Published - 2009

Keywords

Medicinal and Biomolecular Chemistry
Biologically Active Molecules
Organic Chemical Synthesis

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https://hdl.handle.net/1959.11/22918

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abstract = "A series of β-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain.",

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AU - Ayers, Benjamin

AU - Long, Hilary

AU - Sim, Edith

AU - Smellie, Iain A

AU - Wilkinson, Brendan

AU - Fairbanks, Antony J

PY - 2009

Y1 - 2009

N2 - A series of β-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain.

AB - A series of β-arabino glycosyl sulfones with varying alkyl chain lengths were synthesised in a stereoselective fashion as putative mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Biological testing against Mycobacterium bovis BCG revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which was maximal for a C-12 chain.

KW - Medicinal and Biomolecular Chemistry

KW - Biologically Active Molecules

KW - Organic Chemical Synthesis

U2 - 10.1016/j.carres.2009.02.006

DO - 10.1016/j.carres.2009.02.006

M3 - Article

SN - 0008-6215

VL - 344

SP - 739

EP - 746

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 6

ER -

Stereoselective synthesis of β-arabino glycosyl sulfones as potential inhibitors of mycobacterial cell wall biosynthesis

Abstract

Keywords

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