Chemical and chemoenzymatic syntheses of bacillithiol, a unique low molecular weight thiol amongst low G + C Gram positive bacteria

Sunil V. Sharma; Vishnu K. Jothivasan; Gerald L. Newton; Heather Upton; Judy I. Wakabayashi; Melissa G. Kane; Alexandra A. Roberts; Mamta Rawat; James J. La Clair; Chris J. Hamilton

doi:10.1002/anie.201100196

Chemical and chemoenzymatic syntheses of bacillithiol, a unique low molecular weight thiol amongst low G + C Gram positive bacteria

Sunil V. Sharma
, Vishnu K. Jothivasan
, Gerald L. Newton
, Heather Upton
, Judy I. Wakabayashi
, Melissa G. Kane
, Alexandra A. Roberts
, Mamta Rawat
, James J. La Clair
, Chris J. Hamilton

Synthetic and Medicinal Chemistry

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

46 Citations (Scopus)

Abstract

The full monty: The recently discovered thiol cofactor bacillithiol (BSH), its biosynthetic precursors, and its symmetrical disulfide are prepared in two ways. The fosfomycin resistance protein (FosB) is shown to be a BSH-utilizing enzyme. It displays bacillithiol-S-transferase activity with a strong preference for BSH over L-cysteine as its thiol substrate.

Original language	English
Pages (from-to)	7101-7104
Number of pages	4
Journal	Angewandte Chemie-International Edition
Volume	50
Issue number	31
DOIs	https://doi.org/10.1002/anie.201100196
Publication status	Published - 25 Jul 2011

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10.1002/anie.201100196

Cite this

Sharma, S. V., Jothivasan, V. K., Newton, G. L., Upton, H., Wakabayashi, J. I., Kane, M. G., Roberts, A. A., Rawat, M., La Clair, J. J., & Hamilton, C. J. (2011). Chemical and chemoenzymatic syntheses of bacillithiol, a unique low molecular weight thiol amongst low G + C Gram positive bacteria. Angewandte Chemie-International Edition, 50(31), 7101-7104. https://doi.org/10.1002/anie.201100196

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title = "Chemical and chemoenzymatic syntheses of bacillithiol, a unique low molecular weight thiol amongst low G + C Gram positive bacteria",

abstract = "The full monty: The recently discovered thiol cofactor bacillithiol (BSH), its biosynthetic precursors, and its symmetrical disulfide are prepared in two ways. The fosfomycin resistance protein (FosB) is shown to be a BSH-utilizing enzyme. It displays bacillithiol-S-transferase activity with a strong preference for BSH over L-cysteine as its thiol substrate.",

author = "Sharma, \{Sunil V.\} and Jothivasan, \{Vishnu K.\} and Newton, \{Gerald L.\} and Heather Upton and Wakabayashi, \{Judy I.\} and Kane, \{Melissa G.\} and Roberts, \{Alexandra A.\} and Mamta Rawat and \{La Clair\}, \{James J.\} and Hamilton, \{Chris J.\}",

year = "2011",

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Sharma, SV, Jothivasan, VK, Newton, GL, Upton, H, Wakabayashi, JI, Kane, MG, Roberts, AA, Rawat, M, La Clair, JJ & Hamilton, CJ 2011, 'Chemical and chemoenzymatic syntheses of bacillithiol, a unique low molecular weight thiol amongst low G + C Gram positive bacteria', Angewandte Chemie-International Edition, vol. 50, no. 31, pp. 7101-7104. https://doi.org/10.1002/anie.201100196

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AU - Sharma, Sunil V.

AU - Jothivasan, Vishnu K.

AU - Newton, Gerald L.

AU - Upton, Heather

AU - Wakabayashi, Judy I.

AU - Kane, Melissa G.

AU - Roberts, Alexandra A.

AU - Rawat, Mamta

AU - La Clair, James J.

AU - Hamilton, Chris J.

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AB - The full monty: The recently discovered thiol cofactor bacillithiol (BSH), its biosynthetic precursors, and its symmetrical disulfide are prepared in two ways. The fosfomycin resistance protein (FosB) is shown to be a BSH-utilizing enzyme. It displays bacillithiol-S-transferase activity with a strong preference for BSH over L-cysteine as its thiol substrate.

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DO - 10.1002/anie.201100196

M3 - Article

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