Althiomycin

Althiomycin (matamycin) is a thiazole antibiotic, effective against Gram-positive and Gram-negative bacteria. The name matamycin is from "Mata Hari"[1] and the suffix -mycin.

Althiomycin
Names
IUPAC name
N-[2-Hydroxy-1-[4-(3-methoxy-5-oxo-2H-pyrrole-1-carbonyl)-4,5-dihydro-1,3-thiazol-2-yl]ethyl]-2-(nitrosomethylidene)-3H-1,3-thiazole-4-carboxamide
Other names
Altiomycin; Matamycin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • InChI=1S/C16H17N5O6S2/c1-27-8-2-13(23)21(4-8)16(25)11-7-29-15(20-11)9(5-22)19-14(24)10-6-28-12(18-10)3-17-26/h2-3,6,9,11,18,22H,4-5,7H2,1H3,(H,19,24)
    Key: NZGOIHZOTAJJCD-UHFFFAOYSA-N
SMILES
  • COC1=CC(=O)N(C1)C(=O)[C@H]1CSC(=N1)[C@H](CO)NC(=O)C1=CSC(\C=N\O)=N1
Properties
Chemical formula
 C16H17N5O6S2
Molar mass 439.46 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isolated from Streptomyces matensis, the compound was first described by Margalith et al. in 1959.[2] It acts a protein synthesis inhibitor and its site of action is the 50S subunit of the bacterial ribosome.[2]

References
  1. Aronson J (October 1999). "That's show business". BMJ (Clinical Research Ed.). 319 (7215): 972. doi:10.1136/bmj.319.7215.972. PMC 1116803. PMID 10514162.
  2. Pestka S (1975). "Althiomycin". In Corcoran JW, Hahn FE, Snell JF, Arora KL (eds.). Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics. Berlin Heidelberg: Springer-Verlag. pp. 323–6. doi:10.1007/978-3-642-46304-4_21. ISBN 978-3-642-46304-4.
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