JEMA
NOTES: USAGE OF BACILLITHIOL (BSH)
Manufacturer: JEMA Biosciences
P. O. Box 635193
San Diego, CA 92163-5193, U.S.A.
www.jemabiosciences.com

SECTION 1: Product Information
Chemical Name: BSH, Bacillithiol ,2-[[2-[[(2R)-2-amino-3-mercapto-1-oxopropyl]amino]-2-deoxy-α-D-glucopyranosyl]oxy]-(2S)-butanedioic acid
Note: Material is sold as a trifluoracetic acid (TFA) salt. This material is sold as its TFA to assist in stabilization (prevention of the oxidation to BSSB) as well as solubility.
Product Number: 11-001
CAS Registry Number: 1184928-91-3
Formula: C15H23F3N2O12S
Purity: 98% by Ellman's reagent and NMR analyses
Chemical Family: redox thiol
State: solid
Color: white to off-white
Solubility: Soluble in water -a slightly hazy solution occurs above 30 mg/mL in water at pH~ 2-3

SECTION 2: Note
Storage: Store as solid at -20° C protected from light.
Usage: Dissolve solid BSH in pure analytical grade water to between ≤ 30 mg/mL and store at -20° C protected from light.
Stability: Aqueous solutions will be pH 2-3 and are stable for approximately two weeks at -20° C [determined by spectrophotometric thiol titration with Ellman’s reagent]. After storage of the aqueous solution at -18° C for one month, approximately 10% oxidation may be observed. In aqueous solutions at alkaline pH (pH >7), BSH rapidly oxidises to the disulfide BSSB.
Manufacture: Samples of BSH were prepared either by chemical synthesis or chemoenzymatically. The method of preparation is noted in the batch number by TS (chemical synthesis) or CS (chemoenzymatically).

SECTION 3: Publications
Isolation: Newton GL, Rawat M, La Clair JJ, Jothivasan VK, Budiarto T, Hamilton CJ, Claiborne A, Helmann JD, Fahey RC. Bacillithiol is an antioxidant thiol produced in Bacilli. Nat Chem Biol. 2009 Sep;5(9):625-7.
Biosynthesis: Gaballa A, Newton GL, Antelmann H, Parsonage D, Upton H, Rawat M, Claiborne A, Fahey RC, Helmann JD. Biosynthesis and functions of bacillithiol, a major low-molecular-weight thiol in Bacilli. Proc Natl Acad Sci U S A. 2010 Apr 6;107(14):6482-6.
Chemical synthesis: Sharma SV, Jothivasan VK, Newton GL, Upton H, Wakabayashi JI, Kane MG, Roberts AA, Rawat M, La Clair JJ, Hamilton CJ. Chemical and Chemoenzymatic Syntheses of Bacillithiol: A Unique Low-Molecular-Weight Thiol amongst Low G + C Gram-Positive Bacteria. Angew Chem Int Ed Engl. 2011 Jul 25;50(31):7101-4.
Chemoenzymatic synthesis: Sharma SV, Jothivasan VK, Newton GL, Upton H, Wakabayashi JI, Kane MG, Roberts AA, Rawat M, La Clair JJ, Hamilton CJ. Chemical and Chemoenzymatic Syntheses of Bacillithiol: A Unique Low-Molecular-Weight Thiol amongst Low G + C Gram-Positive Bacteria. Angew Chem Int Ed Engl. 2011 Jul 25;50(31):7101-4.

SECTION 4: Other Information
Disclaimer: The information herein is believed to be reliable as of the date compiled. JEMA Biosciences makes no warranty, or guarantee of any kind with respect to the information contained hereinor any use of the product based on this information.
Preparation Date: 8/12/2011
Revision Date: 10/18/2011