Synthetic Studies in the Didemnin Series

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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Sanborn, Alexandra Jan

Contributors dc:contributor

• Rinehart, Kenneth L., Jr.

• Health Sciences, Pharmacology

Language dc:language

eng

Identifier

(MiAaPQ)AAI9834737

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84403