Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

Kajitha Suthagar; Andrew J A Watson; Brendan Wilkinson; Antony J Fairbanks

doi:10.1016/j.ejmech.2015.07.050

Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

Kajitha Suthagar, Andrew J A Watson, Brendan Wilkinson, Antony J Fairbanks

School of Chemistry

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

8 Citations (Scopus)

Abstract

A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain.

Original language	English
Pages (from-to)	153-166
Number of pages	14
Journal	European Journal of Medicinal Chemistry
Volume	102
DOIs	https://doi.org/10.1016/j.ejmech.2015.07.050
Publication status	Published - 18 Sep 2015

Keywords

Arabinose
Carbohydrates
Furanosides
Mycobacteria
Pyranosides
Sulfamides
Tuberculosis

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10.1016/j.ejmech.2015.07.050

Cite this

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title = "Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis",

abstract = "A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain. ",

keywords = "Arabinose, Carbohydrates, Furanosides, Mycobacteria, Pyranosides, Sulfamides, Tuberculosis",

author = "Kajitha Suthagar and Watson, {Andrew J A} and Brendan Wilkinson and Fairbanks, {Antony J}",

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journal = "European Journal of Medicinal Chemistry",

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AU - Suthagar, Kajitha

AU - Watson, Andrew J A

AU - Wilkinson, Brendan

AU - Fairbanks, Antony J

PY - 2015/9/18

Y1 - 2015/9/18

N2 - A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain.

AB - A series of arabinose glycosyl sulfamides with varying alkyl chain types and lengths were synthesised as mimics of decaprenolphosphoarabinose (DPA), and as potential inhibitors of mycobacterial cell wall biosynthesis. Unprecedented conversion of the desired furanose to the thermodynamically more stable pyranose form occurred during final de-protection. Biological testing against Mycobacterium smegmatis revealed low to moderate anti-mycobacterial activity with marked dependence on alkyl chain length, which in the case of mono-substituted sulfamides was maximal for a C-10 chain.

KW - Arabinose

KW - Carbohydrates

KW - Furanosides

KW - Mycobacteria

KW - Pyranosides

KW - Sulfamides

KW - Tuberculosis

U2 - 10.1016/j.ejmech.2015.07.050

DO - 10.1016/j.ejmech.2015.07.050

M3 - Article

VL - 102

SP - 153

EP - 166

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -