82517-08-6

Basic information

• Product Name: 4-Hydroxytetramycin A
• Synonyms: 24-Demethyl-24-ethyl-4-hydroxytetrin A;4-Hydroxytetramycin A;Tetramycin B
• CAS NO: 82517-08-6
• Molecular Formula: C₃₅H₅₃NO₁₄
• Molecular Weight: 711.79362
• Mol File: 82517-08-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Hydroxytetramycin A(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxytetramycin A(82517-08-6)
• EPA Substance Registry System: 4-Hydroxytetramycin A(82517-08-6)

Safety Data

• Hazardous Substances Data: 82517-08-6(Hazardous Substances Data)

Upstream product

• 11076-50-9 tetramycin A 

Relevant articles and documents

Genome Mining of the Biosynthetic Gene Cluster of the Polyene Macrolide Antibiotic Tetramycin and Characterization of a P450 Monooxygenase Involved in the Hydroxylation of the Tetramycin B Polyol Segment

A polyene macrolide antibiotic tetramycin biosynthetic gene cluster was identified by genome mining and isolated from Streptomyces hygrospinosus var. beijingensis. Genetic and in silico analyses gave insights into the mechanism of biosynthesis of tetramycin, and a model of the tetramycin biosynthetic pathway is proposed. Inactivation of a cytochrome P450 monooxygenase gene, tetrK, resulted in the production of a tetramycin B precursor: tetramycin A, which lacks a hydroxy group in its polyol region. TetrK was subsequently overexpressed heterologously in E. coli with a His6 tag, and purified TetrK efficiently hydroxylated tetramycin A to afford tetramycin B. Kinetic studies revealed no inhibition of TetrK by substrate or product. Surprisingly, sequence-alignment analysis showed that TetrK, as a hydroxylase, has much higher homology with epoxidase PimD than with hydroxylases NysL and AmphL. The 3D structure of TetrK was then constructed by homology modeling with PimD as reference. Although TetrK and PimD catalyzed different chemical reactions, homology modeling indicated that they might share the same catalytic sites, despite also possessing some different sites correlated with substrate binding and substrate specificity. These findings offer good prospects for the production of improved antifungal polyene analogues.

TETRAMYCIN B, A NEW POLYENE MACROLIDE ANTIBIOTIC THE STRUCTURE OF TETRAMYCINS A AND B AS STUDIED BY HIGH-FIELD NMR SPECTROSCOPY

The complete assignment os 13C and 400 MHz proton NMR spectra provides corroboration for earlier structural proposals for tetramycin (tetramycin A), a tetraene macrolide antibiotic, and settles the sructure of tetramycin B, a newly isolated congener, as 4-hydroxytetramycin A.