Uniform TitleArabinofuranose 1-deoxy-β-1-C-sulfonic acid
NameWon, Walter S. (author), Cotter, Martha (chair), Knapp, Spencer (internal member), Seidel, Daniel (outside member), Roth, Heinz (outside member), Rutgers University, Graduate School - New Brunswick,
SubjectChemistry and Chemical Biology,
DescriptionUtilizing the tools of bioisosteres, we were able to rationally design a sulfonic acid that can possibly mimic the natural arabinosyltransferase donor, β-1,2-cis-decaprenolphoarabinose. The sulfur replacement provides a more enzymatically stable donor that can possibly inhibit the actions of arabinosyltransferases upon binding and thus prevent the biosynthetic pathway of the arabinogalactan cell wall that is essential to the viability of Mycobacterium tuberculosis. We have successfully synthesized β-1-C-sulfonic acid from a new 1-thio-D-arabinofuanose acetate. Incorporating the ideas from previously published routes to the key intermediates, we describe the successes and failures in our approach to the target sulfonic acid. The route includes a useful method of oxidizing acid-sensitive substrates.
NoteIncludes bibliographical references (p. 23-24).
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.