Biosynthetic Intermediates of the Tetradehydro Cyclic Dipeptide Albonoursin Produced by Streptomyces albulus KO-23.

Hiroshi Kanzaki, Satohiro Yanagisawa, Teruhiko Nitoda

Research output: Contribution to journal › Article

23 Citations (Scopus)

Abstract

The cell-free extract of an albonoursin-producing strain <i>Streptomyces albulus</i> KO-23 catalyzes the conversion of cyclo(L-Leu-L-Phe) (<b>1</b>) to albonoursin (<b>2</b>). At the early stage of this conversion, two compounds were newly formed prior to albonoursin synthesis in the reaction mixture. These compounds were isolated and identified as (<i>Z</i>)-3-benzylidene-6-isobutyl-2, 5-piperazinedione (<b>4</b>) and (<i>Z</i>)-3-benzyl-6-isobutylidene-2, 5-piperazineclione (<b>3</b>). The cell-free extract also catalyzed the conversion of compound <b>3</b> or <b>4</b> to albonoursin. From these results, albonoursin was found to be biosynthesized <i>via</i> these compounds from cyclo(L-Leu-L-Phe). These didehydro diketopiperazines exhibited no inhibitory activity toward the first cleavage of sea urchin embryo in contrast to the higher cytotoxicity for albonoursin, indicating that dehydrogenation at α, β-positions of both amino acid residues in diketopiperazines is required for cytotoxicity.
Original languageEnglish
Pages (from-to)1257-1264
Number of pages8
JournalJournal of Antibiotics
Volume53
Issue number11
DOIs
Publication statusPublished - Nov 25 2000
Externally publishedYes

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Dipeptides
Streptomyces
Diketopiperazines
3,6-bis(5-chloro-2-piperidyl)-2,5-piperazinedione
Cell Extracts
Sea Urchins
albonoursin
Embryonic Structures
Amino Acids

Cite this

Biosynthetic Intermediates of the Tetradehydro Cyclic Dipeptide Albonoursin Produced by Streptomyces albulus KO-23. / Kanzaki, Hiroshi; Yanagisawa, Satohiro; Nitoda, Teruhiko.

In: Journal of Antibiotics, Vol. 53, No. 11, 25.11.2000, p. 1257-1264.

Research output: Contribution to journal › Article

Kanzaki, H, Yanagisawa, S & Nitoda, T 2000, 'Biosynthetic Intermediates of the Tetradehydro Cyclic Dipeptide Albonoursin Produced by Streptomyces albulus KO-23.', Journal of Antibiotics, vol. 53, no. 11, pp. 1257-1264. https://doi.org/10.7164/antibiotics.53.1257
Kanzaki H, Yanagisawa S, Nitoda T. Biosynthetic Intermediates of the Tetradehydro Cyclic Dipeptide Albonoursin Produced by Streptomyces albulus KO-23. Journal of Antibiotics. 2000 Nov 25;53(11):1257-1264. https://doi.org/10.7164/antibiotics.53.1257
Kanzaki, Hiroshi ; Yanagisawa, Satohiro ; Nitoda, Teruhiko. / Biosynthetic Intermediates of the Tetradehydro Cyclic Dipeptide Albonoursin Produced by Streptomyces albulus KO-23. In: Journal of Antibiotics. 2000 ; Vol. 53, No. 11. pp. 1257-1264.
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abstract = "The cell-free extract of an albonoursin-producing strain Streptomyces albulus KO-23 catalyzes the conversion of cyclo(L-Leu-L-Phe) (1) to albonoursin (2). At the early stage of this conversion, two compounds were newly formed prior to albonoursin synthesis in the reaction mixture. These compounds were isolated and identified as (Z)-3-benzylidene-6-isobutyl-2, 5-piperazinedione (4) and (Z)-3-benzyl-6-isobutylidene-2, 5-piperazineclione (3). The cell-free extract also catalyzed the conversion of compound 3 or 4 to albonoursin. From these results, albonoursin was found to be biosynthesized via these compounds from cyclo(L-Leu-L-Phe). These didehydro diketopiperazines exhibited no inhibitory activity toward the first cleavage of sea urchin embryo in contrast to the higher cytotoxicity for albonoursin, indicating that dehydrogenation at α, β-positions of both amino acid residues in diketopiperazines is required for cytotoxicity.",
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N2 - The cell-free extract of an albonoursin-producing strain Streptomyces albulus KO-23 catalyzes the conversion of cyclo(L-Leu-L-Phe) (1) to albonoursin (2). At the early stage of this conversion, two compounds were newly formed prior to albonoursin synthesis in the reaction mixture. These compounds were isolated and identified as (Z)-3-benzylidene-6-isobutyl-2, 5-piperazinedione (4) and (Z)-3-benzyl-6-isobutylidene-2, 5-piperazineclione (3). The cell-free extract also catalyzed the conversion of compound 3 or 4 to albonoursin. From these results, albonoursin was found to be biosynthesized via these compounds from cyclo(L-Leu-L-Phe). These didehydro diketopiperazines exhibited no inhibitory activity toward the first cleavage of sea urchin embryo in contrast to the higher cytotoxicity for albonoursin, indicating that dehydrogenation at α, β-positions of both amino acid residues in diketopiperazines is required for cytotoxicity.

AB - The cell-free extract of an albonoursin-producing strain Streptomyces albulus KO-23 catalyzes the conversion of cyclo(L-Leu-L-Phe) (1) to albonoursin (2). At the early stage of this conversion, two compounds were newly formed prior to albonoursin synthesis in the reaction mixture. These compounds were isolated and identified as (Z)-3-benzylidene-6-isobutyl-2, 5-piperazinedione (4) and (Z)-3-benzyl-6-isobutylidene-2, 5-piperazineclione (3). The cell-free extract also catalyzed the conversion of compound 3 or 4 to albonoursin. From these results, albonoursin was found to be biosynthesized via these compounds from cyclo(L-Leu-L-Phe). These didehydro diketopiperazines exhibited no inhibitory activity toward the first cleavage of sea urchin embryo in contrast to the higher cytotoxicity for albonoursin, indicating that dehydrogenation at α, β-positions of both amino acid residues in diketopiperazines is required for cytotoxicity.

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