Topic
Hitachimycin
About: Hitachimycin is a research topic. Over the lifetime, 4 publications have been published within this topic receiving 47 citations.
Papers
TL;DR: The results suggest that the identified gene cluster in Streptomyces scabrisporus is responsible for the biosynthesis of hitachimycin, including a unique polyketide skeletal transformation mechanism.
Abstract: Hitachimycin is a macrolactam antibiotic with (S)-β-phenylalanine (β-Phe) at the starter position of its polyketide skeleton. To understand the incorporation mechanism of β-Phe and the modification mechanism of the unique polyketide skeleton, the biosynthetic gene cluster for hitachimycin in Streptomyces scabrisporus was identified by genome mining. The identified gene cluster contains a putative phenylalanine-2,3-aminomutase (PAM), five polyketide synthases, four β-amino-acid-carrying enzymes, and a characteristic amidohydrolase. A hitA knockout mutant showed no hitachimycin production, but antibiotic production was restored by feeding with (S)-β-Phe. We also confirmed the enzymatic activity of the HitA PAM. The results suggest that the identified gene cluster is responsible for the biosynthesis of hitachimycin. A plausible biosynthetic pathway for hitachimycin, including a unique polyketide skeletal transformation mechanism, is proposed.
34 citations
TL;DR: Several acyl derivatives of hitachimycin have been synthesized and their activities, including antibacterial, cytocidal against HeLa cells and in vivo antitumor against sarcoma 180, evaluated.
Abstract: Several acyl derivatives of hitachimycin have been synthesized and their activities, including antibacterial, cytocidal against HeLa cells and in vivo antitumor against sarcoma 180, evaluated. Some of these derivatives showed higher antitumor activity than hitachimycin. Among the derivatives, 11-O-propionyl-15-O-butyrylhitachimycin (12) and the 11-O-acylhitachimycins (15-17) were most effective in in vivo assay.
11 citations
TL;DR: Several carbonate derivatives of hitachimycin have been synthesized and evaluated their activities including antibacterial, cytocidal against HeLa cells and in vivo antitumor against Sarcoma 180, where 11,15-di-O-methoxycarbonylhitachimYcin was most effective in in vivo assay.
Abstract: Several carbonate derivatives of hitachimycin have been synthesized and evaluated their activities including antibacterial, cytocidal against HeLa cells and in vivo antitumor against Sarcoma 180. Some of these derivatives showed higher antitumor activity than hitachimycin. Among the derivatives, 11,15-di-O-methoxycarbonylhitachimycin (2), 11,15-di-O-ethoxycarbonylhitachimycin (3) and 15-O-methoxycarbonylhitachimycin (9) were most effective in in vivo assay.
7 citations
TL;DR: Amino acyl derivatives of hitachimycin have been synthesized and evaluated their activities including antibacterial, cytocidal against HeLa cells and in vivo antitumor against sarcoma 180 and the solubility of these compounds was improved.
Abstract: Amino acyl derivatives of hitachimycin have been synthesized and evaluated their activities including antibacterial, cytocidal against HeLa cells and in vivo antitumor against sarcoma 180. 15-O-(tert-Butoxycarbonyl(BOC)-glycyl)hitachimycin (2), 15-O-(BOC-beta-alanyl)hitachimycin (4), 15-O-(BOC-(O-tert-Bu)-glutamyl)hitachimycin (6) and 15-O-L-alanylhitachimycin (11) showed comparable in vivo antitumor activity with hitachimycin and the solubility of these compounds was improved.
5 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2015 | 1 |
| 1989 | 2 |
| 1988 | 1 |