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

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 we...

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Bibliographic Details
Published in:Journal of antibiotics 2000/11/25, Vol.53(11), pp.1257-1264
Main Authors: KANZAKI, HIROSHI, YANAGISAWA, SATOHIRO, NITODA, TERUHIKO
Format: Article
Language:English
Subjects:
Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
Biological and medical sciences
Cell Survival - drug effects
Cell-Free System
Embryo, Nonmammalian - cytology
Embryo, Nonmammalian - drug effects
General pharmacology
Medical sciences
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Piperazines - chemistry
Piperazines - metabolism
Piperazines - pharmacology
Sea Urchins - embryology
Spectrum Analysis
Streptomyces - chemistry
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.53.1257