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Synthesis and testing the intermediacy of diketopiperazines in the biosynthesis of ecteinascidins

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Date Issued:
2000
Summary:
Ecteinascidin 743 is a trace secondary metabolite isolated from the marine tunicate, Ecteinascidia turbinata. Ecteinacidin 743 a most potent antitumor agent, is currently in Phase II clinical trials in Europe and in the USA. A cell-free extract of Ecteinascidia turbinata was used to investigate the biogenetic origin of the ecteinascidins. Incubation experiments with radiolabeled diketopiperazines indicated that the diketopiperazine of tyrosine is the first committed intermediate in the biosynthesis of ecteinascidins. Phenylalanine diketopiperazine was not transformed into the ecteinascidins indicating that this cyclic dipeptide is not an intermediate in the biosynthesis of ecteinascidins. The diketopiperazine of DOPA was used as a cold carrier demonstrating that the diketopiperazine of tyrosine is oxidized to DOPA diketopiperazine and then further transformed to the ecteinascidins.
Title: Synthesis and testing the intermediacy of diketopiperazines in the biosynthesis of ecteinascidins.
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Name(s): Jeedigunta, Shanti
Florida Atlantic University, Degree grantor
Kerr, Russell G., Thesis advisor
Charles E. Schmidt College of Science
Department of Chemistry and Biochemistry
Type of Resource: text
Genre: Electronic Thesis Or Dissertation
Issuance: monographic
Date Issued: 2000
Publisher: Florida Atlantic University
Place of Publication: Boca Raton, FL
Physical Form: application/pdf
Extent: 99 p.
Language(s): English
Summary: Ecteinascidin 743 is a trace secondary metabolite isolated from the marine tunicate, Ecteinascidia turbinata. Ecteinacidin 743 a most potent antitumor agent, is currently in Phase II clinical trials in Europe and in the USA. A cell-free extract of Ecteinascidia turbinata was used to investigate the biogenetic origin of the ecteinascidins. Incubation experiments with radiolabeled diketopiperazines indicated that the diketopiperazine of tyrosine is the first committed intermediate in the biosynthesis of ecteinascidins. Phenylalanine diketopiperazine was not transformed into the ecteinascidins indicating that this cyclic dipeptide is not an intermediate in the biosynthesis of ecteinascidins. The diketopiperazine of DOPA was used as a cold carrier demonstrating that the diketopiperazine of tyrosine is oxidized to DOPA diketopiperazine and then further transformed to the ecteinascidins.
Identifier: 9780599596818 (isbn), 15754 (digitool), FADT15754 (IID), fau:12507 (fedora)
Degree granted: Thesis (M.S.)--Florida Atlantic University, 2000.
Collection: FAU Electronic Theses and Dissertations Collection
Note(s): Charles E. Schmidt College of Science
Subject(s): Sea squirts
Dopa
Tunicata
Held by: Florida Atlantic University Libraries
Persistent Link to This Record: http://purl.flvc.org/fcla/dt/15754
Sublocation: Digital Library
Use and Reproduction: Copyright © is held by the author with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Use and Reproduction: http://rightsstatements.org/vocab/InC/1.0/
Host Institution: FAU
Is Part of Series: Florida Atlantic University Digital Library Collections.