Chemistry:Tomaymycin

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Tomaymycin
Tomaymycin.svg
Names
IUPAC name
(6R,6aS,8Z)-8-ethylidene-3-hydroxy-2,6-dimethoxy-6,6a,7,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one[1]
Other names
GNF-Pf-1072[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
Properties
C16H20N2O4
Molar mass 304.346 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

Tomaymycin is an antitumor and antibiotic pyrrolobenzodiazepine with the molecular formula C16H20N2O4.[2][1][3][4] Tomaymycin is produced by the bacterium Streptomyces achromogenes.[2]

References

  1. 1.0 1.1 1.2 "Tomaymycin" (in en). Pubchem.ncbi.NLM.nih.gov. https://pubchem.ncbi.nlm.nih.gov/compound/Tomaymycin#section=3D-Conformer. 
  2. 2.0 2.1 Li, Wei; Chou, ShenChieh; Khullar, Ankush; Gerratana, Barbara (May 2009). "Cloning and Characterization of the Biosynthetic Gene Cluster for Tomaymycin, an SJG-136 Monomeric Analog". Applied and Environmental Microbiology 75 (9): 2958–2963. doi:10.1128/AEM.02325-08. PMID 19270147. Bibcode2009ApEnM..75.2958L. 
  3. von Tesmar, Alexander; Hoffmann, Michael; Pippel, Jan; Fayad, Antoine Abou; Dausend-Werner, Stefan; Bauer, Armin; Blankenfeldt, Wulf; Müller, Rolf (October 2017). "Total Biosynthesis of the Pyrrolo[4,2]benzodiazepine Scaffold Tomaymycin on an In Vitro Reconstituted NRPS System". Cell Chemical Biology 24 (10): 1216–1227.e8. doi:10.1016/j.chembiol.2017.08.001. PMID 28890318. 
  4. Tomaymycin | Antitumor Antibiotic | MedChemExpress. https://www.medchemexpress.com/tomaymycin.html?locale=de-DE?src=google-product&gclid=EAIaIQobChMInZezuKO29wIVhBB9Ch1w0Q9-EAAYASAAEgKRe_D_BwE. 

Further reading

  • Szeinbach, Sheryl Lynn (1983) (in en). The Genetic Activity of Anthramycin, Tomaymycin and Sibiromycin in Bacterial Forward- and Reverse-mutation Assays and in the Mouse Bone-marrow Micronucleus Test. University of Kentucky. 
  • Corcoran, John W. (6 December 2012) (in en). Biosynthesis. Springer Science & Business Media. p. 290. ISBN 978-3-642-67724-3. 
  • Benedetti, Françoise; Perrin, Marc-Antoine; Bosc, Sebastien; Chouteau, Franck; Champion, Nicolas; Bigot, Antony (15 May 2020). "Total Synthesis of (+)-Oxo-tomaymycin". Organic Process Research & Development 24 (5): 762–768. doi:10.1021/acs.oprd.0c00009.