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ysu1347888245.pdf (2.08 MB)
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Chemical and Biochemical Studies of Bacillithiol
Author Info
Russell, Janelle P.N.
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1347888245
Abstract Details
Year and Degree
2012, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
Abstract
Bacillithiol (BSH), the α-anomeric glycoside of L-cysteinyl-D-glucosamine with L-malic acid, is the recently identified low-molecular-weight (LMW) thiol in low G + C content Gram-positive bacteria. Although BSH has not been fully characterized it is thought to have functions analogous to those of glutathione, the major LMW thiol present in eukaryotes. Glutathione is known to act as an antioxidant and functions to protect the cell against oxidation and other toxins. BSH has been shown to contribute to the detoxification of toxic compounds including some antibiotics. Since bacillithiol is not present in humans its metabolism presents novel targets for antibacterial drug therapies. An attempt was made to chemically synthesize BSH for its use in biochemical studies that would further elucidate its functions. The trichloroacetimidate method was employed for the introduction of the α-glycosidic bond linking D-glucosamine with an L-malic acid derivative. A cysteine derivative was prepared with a pentafluorophenyl group activating it for peptide bond formation with D-glucosamine. NMR and IR spectroscopy were used to confirm the synthesis of these compounds. Efforts made toward forming the peptide bond without the use of a peptide coupling reagent were unsuccessful.
Committee
Nina V. Stourman, Ph.D. (Advisor)
Michael A. Serra, Ph.D. (Committee Member)
Peter Norris, Ph.D. (Committee Member)
Pages
69 p.
Subject Headings
Biochemistry
Keywords
bacillithiol
;
low-molecular-weight thiols
;
reactive oxygen species
;
trichloroacetimidate
;
glycosylation
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RIS
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Citations
Russell, J. P.N. (2012).
Chemical and Biochemical Studies of Bacillithiol
[Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1347888245
APA Style (7th edition)
Russell, Janelle.
Chemical and Biochemical Studies of Bacillithiol.
2012. Youngstown State University, Master's thesis.
OhioLINK Electronic Theses and Dissertations Center
, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1347888245.
MLA Style (8th edition)
Russell, Janelle. "Chemical and Biochemical Studies of Bacillithiol." Master's thesis, Youngstown State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1347888245
Chicago Manual of Style (17th edition)
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Document number:
ysu1347888245
Download Count:
483
Copyright Info
© 2012, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.