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Title:Synthetic Studies in the Didemnin Series
Author(s):Sanborn, Alexandra Jan
Doctoral Committee Chair(s):Rinehart, Kenneth L., Jr.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Health Sciences, Pharmacology
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.
Issue Date:1998
Description:413 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1998.
Other Identifier(s):(MiAaPQ)AAI9834737
Date Available in IDEALS:2015-09-25
Date Deposited:1998

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