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Studies towards the Synthesis of Analogs of Bacillithiol

Adesoye, Olumuyiwa Gbenga
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1338764980

Abstract Details

2012, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
Low molecular weight thiols relieve oxidative stress by forming disulfide bonds and reduce alkylating agents such as xenobiotics to less harmful adducts by the action of thiol-dependent S-tranferases. In some Gram-positive bacteria such as Bacillus subtilis, bacillithiol (BSH) has been identified as the major low molecular weight thiol. The synthesis of a BSH analog that will interact with and inactivate BSH-dependent enzymes is therefore of interest. BSH is an α-anomeric glycoside of L-cysteinyl-D-glucosamine with L-malic acid. Normal and inverse glycosylation procedures are employed and solvation effects are investigated to achieve the synthesis of BSH analogs. Reaction products are analyzed and characterized by thin layer chromatography and nuclear magnetic resonance spectroscopy. The syntheses of D-glucopyranosyl dimethyl malate ester (2), α-D-glucopyranosyl dimethyl malate ester (10) and β-D-glucopyranosyl dimethyl malate ester (12) as protected analogs of BSH are herein reported.
Peter Norris, PhD (Advisor)
Nina Stourman, PhD (Committee Member)
John Jackson, PhD (Committee Member)
121 p.
Chemistry
Low molecular weight thiols; bacillithiol; fosfomycin; glycosylation

Recommended Citations

Citations

  • Adesoye, O. G. (2012). Studies towards the Synthesis of Analogs of Bacillithiol [Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1338764980

    APA Style (7th edition)

  • Adesoye, Olumuyiwa. Studies towards the Synthesis of Analogs of Bacillithiol. 2012. Youngstown State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1338764980.

    MLA Style (8th edition)

  • Adesoye, Olumuyiwa. "Studies towards the Synthesis of Analogs of Bacillithiol." Master's thesis, Youngstown State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1338764980

    Chicago Manual of Style (17th edition)

ysu1338764980
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© 2012, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.