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Total synthesis and biological evaluation of transvalencin Z.
- Source :
-
Journal of natural products [J Nat Prod] 2012 Jun 22; Vol. 75 (6), pp. 1037-43. Date of Electronic Publication: 2012 May 22. - Publication Year :
- 2012
-
Abstract
- The emerging global epidemic of drug-resistant tuberculosis has created an urgent need to identify novel therapeutic approaches for disease treatment. Transvalencin Z (1) is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure-activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a-d), and the absolute configurations were defined using chemical synthesis, HPLC retention times, and optical rotation measurements. Surprisingly, none of the transvalencin Z diastereomers exhibited any inhibitory activity against a panel of microbial pathogens, including several species of mycobacteria.
- Subjects :
- Acinetobacter baumannii drug effects
Animals
Anti-Bacterial Agents chemistry
Bacillus subtilis drug effects
Candida albicans drug effects
Chlorocebus aethiops
Chromatography, High Pressure Liquid
Enterococcus faecalis drug effects
Escherichia coli drug effects
Klebsiella pneumoniae drug effects
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium drug effects
Nocardia chemistry
Oxazoles chemistry
Pseudomonas aeruginosa drug effects
Salicylates chemistry
Staphylococcus aureus drug effects
Anti-Bacterial Agents chemical synthesis
Anti-Bacterial Agents pharmacology
Oxazoles chemical synthesis
Oxazoles pharmacology
Salicylates chemical synthesis
Salicylates pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 75
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 22616579
- Full Text :
- https://doi.org/10.1021/np200972s