Abstract
(-)-Indolactam-V (1) without a hydrophobic chain at positions 6 and 7 of the indole ring is a weak tumor promoter compared with teleocidin Bs. To investigate the effects of the hydrophobic substituent at position 6 of teleocidin Bs, we synthesized (-)-6-n-octyl-indolactam-V (2) by a palladium-catalyzed coupling reaction from (-)-6-bromo-indolactam-V (7) which had been obtained by microbial conversion with Streptoverticillium blastmyceticum NA34-17 as the key step. (-)-7-n-Octyl-indolactam-V (3) with potent biological activities comparable to those of teleocidin Bs was similarly synthesized from (-)-7-bromo-indolactam-V as a positive control. Compound 2 showed similar biological activities to those of 3, indicating that the effect of the hydrophobic substituent at position 6 of 1 was identical to that at position 7.
Original language | English |
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Pages (from-to) | 1568-1573 |
Number of pages | 6 |
Journal | Bioscience, Biotechnology and Biochemistry |
Volume | 62 |
Issue number | 8 |
DOIs | |
Publication status | Published - Jan 1 1998 |
Externally published | Yes |
Keywords
- (-)-6-n-octyl-indolactam-V
- Epstein-Barr virus
- Protein kinase C
- Teleocidin
- Tumor promoter
ASJC Scopus subject areas
- Biotechnology
- Analytical Chemistry
- Biochemistry
- Applied Microbiology and Biotechnology
- Molecular Biology
- Organic Chemistry