Myxothiazole

Structural formula
General
Surname	Myxothiazole
Molecular formula	C 25 H 33 N 3 O 3 S 2
External identifiers / databases
EC number	622-464-9
ECHA InfoCard	100.151.224
PubChem	6437357
ChemSpider	4941921
DrugBank	DB04741
Wikidata	Q6949371
properties
Molar mass	487.68 g mol −1
Physical state	firmly
solubility	slightly soluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300
	P: 264-301 + 310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Myxothiazole is a strong antifungal antibiotic . The compound specifically inhibits cytochrome c reductase in the respiratory chain at the Q _o center. In contrast to stigmatellin , myxothiazole does not form a hydrogen bond to the Rieske iron-sulfur protein.

The bi thiazole system is formed from cysteine in the biosynthesis .

Hans Reichenbach (GBF Braunschweig) succeeded in isolating myxothiazole from the myxobacterium Myxococcus fulvus in the 1970s . With this, Gebhard von Jagow (University of Munich) succeeded in blocking the respiratory chain exactly where the electrons from the ubiquinone flow in the direction of oxygen; the second way could be sealed off with the antibiotic antimycin A.

Individual evidence

↑ ^a ^b ^c Entry for CAS no. 76706-55-3 in the GESTIS substance database of the IFA , accessed on December 30, 2015 (JavaScript required)
↑ Wolfram Troxitzsch-Kienast, Victor Wray, Klaus Gerth, Hans Reichenbach, Gerhard Höfle: Antibiotics from sliding bacteria, XXVIII. Biosynthesis of myxothiazole in Myxococcus fulvus Mx f16 . In: Liebig's annals of chemistry . No. 1 , January 14, 1986, p. 93-98 , doi : 10.1002 / jlac.198619860109 ( PDF ).
^ Georg Thierbach, Hans Reichenbach: Myxothiazol, a new antibiotic interfering with respiration . In: Antimicrobial Agents and Chemotherapy . tape 19 , no. 4 , April 1981, pp. 504-507 , PMID 7247372 , PMC 181466 (free full text).
↑ Gebhard von Jagow, WD Engel: Complete Inhibition of Electron Transfer from Ubiquinol to Cytochrome by the Combined Action of Antimycin and Myxothiazol . In: FEBS Letters . tape 136 , no. 1 , December 1981, pp. 19-24 , doi : 10.1016 / 0014-5793 (81) 81206-9 ( PDF ).

[GESTIS-1] Entry for CAS no. 76706-55-3 in the GESTIS substance database of the IFA , accessed on December 30, 2015 (JavaScript required)

[bio-2] Wolfram Troxitzsch-Kienast, Victor Wray, Klaus Gerth, Hans Reichenbach, Gerhard Höfle: Antibiotics from sliding bacteria, XXVIII. Biosynthesis of myxothiazole in Myxococcus fulvus Mx f16 . In: Liebig's annals of chemistry . No. 1 , January 14, 1986, p. 93-98 , doi : 10.1002 / jlac.198619860109 ( PDF ).

[3] Georg Thierbach, Hans Reichenbach: Myxothiazol, a new antibiotic interfering with respiration . In: Antimicrobial Agents and Chemotherapy . tape 19 , no. 4 , April 1981, pp. 504-507 , PMID 7247372 , PMC 181466 (free full text).

[4] Gebhard von Jagow, WD Engel: Complete Inhibition of Electron Transfer from Ubiquinol to Cytochrome by the Combined Action of Antimycin and Myxothiazol . In: FEBS Letters . tape 136 , no. 1 , December 1981, pp. 19-24 , doi : 10.1016 / 0014-5793 (81) 81206-9 ( PDF ).