539-35-5

Basic information

• Product Name: mycobacidin
• Synonyms: mycobacidin;Acidomycin;Cinnamonin;PA-95;Thiazolidone antibiotic;6-(4-ketothiazolidin-2-yl)hexanoic acid;6-(4-oxo-1,3-thiazolidin-2-yl)hexanoic acid
• CAS NO: 539-35-5
• Molecular Formula: C₉H₁₅NO₃S
• Molecular Weight: 217.288
• Mol File: 539-35-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 495.6°Cat760mmHg
• Flash Point: 253.5°C
• Appearance: /
• Density: 1.2447 (rough estimate)
• Vapor Pressure: 3.58E-11mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• CAS DataBase Reference: mycobacidin(CAS DataBase Reference)
• NIST Chemistry Reference: mycobacidin(539-35-5)
• EPA Substance Registry System: mycobacidin(539-35-5)

Safety Data

• Hazardous Substances Data: 539-35-5(Hazardous Substances Data)

Usage

Purification Methods

The dl-form is dimorphic; it crystallises from CHCl3 with m 116-117o, and from H2O with m 123o. The l(-)-enantiomer (from Actinomyces) crystallises from H2O, MeOH (m 139-140o), aqueous EtOH (m 140-141o) or EtOAc, and has [] D 20 -54o (c 1, MeOH). The d(+)-enantiomer (from optical resolution of the brucine salt) has m 138-139o (from H2O) and [] D 25 +57o (c 1, MeOH). The optically active acids racemise in hot alkali. [McLamore et al. J Am Chem Soc 75 105 1953, Beilstein 27 III/IV 4281.]

InChI:InChI=1/C9H15NO3S/c11-7-6-14-8(10-7)4-2-1-3-5-9(12)13/h8H,1-6H2,(H,10,11)(H,12,13)

Upstream product

• 539-87-7 oxocan-2-one 
• 14565-11-8 methyl 7-hydroxyheptanoate 
• 6032-95-7 methyl 6-(4-oxothiazolidin-2-yl)hexanoate 
• 502-42-1 cycloheptanone 

Downstream Products

• 35923-65-0 6-formyl hexanoic acid 

Relevant articles and documents

Investigation of (S)-(-)-acidomycin: A selective antimycobacterial natural product that inhibits biotin synthase

The synthesis, absolute stereochemical configuration, complete biological characterization, mechanism of action and resistance, and pharmacokinetic properties of (S)-(-)-acidomycin are described. Acidomycin possesses promising antitubercular activity against a series of contemporary drug susceptible and drug-resistant M. tuberculosis strains (minimum inhibitory concentrations (MICs) = 0.096-6.2 μM) but is inactive against nontuberculosis mycobacteria and Gram-positive and Gram-negative pathogens (MICs > 1000 μM). Complementation studies with biotin biosynthetic pathway intermediates and subsequent biochemical studies confirmed acidomycin inhibits biotin synthesis with a Ki of approximately 1 μM through the competitive inhibition of biotin synthase (BioB) and also stimulates unproductive cleavage of S-adenosyl-l-methionine (SAM) to generate the toxic metabolite 5′-deoxyadenosine. Cell studies demonstrate acidomycin selectively accumulates in M. tuberculosis providing a mechanistic basis for the observed antibacterial activity. The development of spontaneous resistance by M. tuberculosis to acidomycin was difficult, and only low-level resistance to acidomycin was observed by overexpression of BioB. Collectively, the results provide a foundation to advance acidomycin and highlight BioB as a promising target.