Nov, 2000
Biosynthetic intermediates of the tetradehydro cyclic dipeptide albonoursin produced by Streptomyces albulus KO-23
JOURNAL OF ANTIBIOTICS
- ,
- ,
- Volume
- 53
- Number
- 11
- First page
- 1257
- Last page
- 1264
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.7164/antibiotics.53.1257
- Publisher
- JAPAN ANTIBIOT RES ASSN
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-piperazinedione (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 alpha,beta -positions of both amino acid residues in diketopiperazines is required for cytotoxicity.
- Link information
- ID information
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- DOI : 10.7164/antibiotics.53.1257
- ISSN : 0021-8820
- Web of Science ID : WOS:000165552700003