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https://hdl.handle.net/2142/84403
Description
Title
Synthetic Studies in the Didemnin Series
Author(s)
Sanborn, Alexandra Jan
Issue Date
1998
Doctoral Committee Chair(s)
Rinehart, Kenneth L., Jr.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Health Sciences, Pharmacology
Language
eng
Abstract
Semi-synthetic studies directed toward didemnin analogues in which structural modifications were introduced in the side chain for investigating structure-activity relationships have been performed. The syntheses of several known didemnins including didemnin M, dehydrodidemnin B, and pyroglutamyl didemnin B have been successfully completed. In addition, several new didemnin analogues have been synthesized including glutaminyl didemnin B, (Ala$\sp3$) didemnin B, (Ala$\sp3$) didemnin M, and various other alaninyl derivatives. A total of forty didemnin analogues (thirty-four of which are new) were prepared semi-synthetically. In vitro cytotoxicity, antiviral activity, and structure-activity relationships for the above compounds are reported. Both glutaminyldidemnin B and (Ala$\sp3$) didemnin B show significantly greater activity against L1210 cells (murine leukemia) than the natural source of didemnin B.
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