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

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

43 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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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.}",

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doi = "10.1002/anie.201100196",

language = "English",

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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

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