Diketopiperazines as advanced intermediates in the ...



Title Diketopiperazines as advanced intermediates in the biosynthesis of ecteinascidins
Author(s) S. Jeedigunta, J. M. Krenisky, Russell G. Kerr, Florida Sea Grant
Related item Tetrahedron
Start page 3303
End page 3307
Date 2000
Abstract The ecteinascidins are a family of tetrahydroisoquinoline alkaloids isolated from the tunicate Ecteinascidia turbinata. Ecteinascidin 743 is a candidate for the treatment of several human cancers. Ecteinascidins have been shown to kill tumor cells in vitro, inhibit tumor growth in vivo, suppress allograft rejection, diminish host reactions to tissue grafts, and inhibit lymphocyte proliferation. The ecteinascidins have two mechanisms of action -- they are unique alkylating agents and also disaggregate microtubule complexes without affecting tubulin itself. In this paper, the diketopiperazines of phenylalanine, tyrosine and DOPA were synthesized from 14 C-labeled amino acids and clarified as intermediates in the biosynthesis of the ecteinascidins.
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