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Towards the Synthesis of a C15-C27 Analog of Okadaic Acid and Second Generation Synthesis of Apratoxin A and Apratoxin Analogs

Wherritt, Daniel John

Abstract Details

2010, Doctor of Philosophy, Ohio State University, Chemistry.
19-epi-okadaic acid is a potent inhibitor of protein phosphatase 2A (PP2A) versus protein phosphatase 1 (PP1) (IC50 = 0.47 nM and IC50 = 465 nM respectively). With 19-epi-okadaic acid’s selectivity for PP2A it would be useful for studying PP2A’s role in many important biological systems. However, only a minimal amount can be isolated and direct synthesis is very difficult. The first part of this dissertation describes attempts at synthesizing a 19-epi-okadiac acid isostere that should maintain 19-epi-okadiac acid’s biological activity. The apratoxin family of natural products, isolated from marine cyanobacterium of the genus Lyngbya, are highly cytotoxic depsipeptides with an unknown mode of action. In 2003 Dr. Jiehao Chen and Professor Forsyth published the first total synthesis of apratoxin A. The second part of this dissertation describes improvements of Dr. Chen’s synthesis and the synthesis of some analogs of apratoxin for structure activity relationship studies.
Craig Forsyth, PhD (Advisor)
Jovica Badjic, PhD (Committee Member)
Dennis Bong, PhD (Committee Member)
Zhongtang Yu, PhD (Committee Member)
219 p.

Recommended Citations

Citations

  • Wherritt, D. J. (2010). Towards the Synthesis of a C15-C27 Analog of Okadaic Acid and Second Generation Synthesis of Apratoxin A and Apratoxin Analogs [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1285698483

    APA Style (7th edition)

  • Wherritt, Daniel. Towards the Synthesis of a C15-C27 Analog of Okadaic Acid and Second Generation Synthesis of Apratoxin A and Apratoxin Analogs. 2010. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1285698483.

    MLA Style (8th edition)

  • Wherritt, Daniel. "Towards the Synthesis of a C15-C27 Analog of Okadaic Acid and Second Generation Synthesis of Apratoxin A and Apratoxin Analogs." Doctoral dissertation, Ohio State University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=osu1285698483

    Chicago Manual of Style (17th edition)