Tomaymycin

Tomaymycin
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
	Other names GNF-Pf-1072
Identifiers
CAS Number	35050-55-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:157681; CHEBI:167318;
ChEMBL	ChEMBL580013;
ChemSpider	13076951;
PubChem CID	12444380;
	InChI InChI=1S/C16H20N2O4/c1-4-9-5-12-15(22-3)17-11-7-13(19)14(21-2)6-10(11)16(20)18(12)8-9/h4,6-7,12,15,17,19H,5,8H2,1-3H3/b9-4-/t12-,15+/m0/s1 Key: UQVNRKBFAXNOGA-OHLDGCSVSA-N;
	SMILES C/C=C\1/C[C@H]2[C@H](NC3=CC(=C(C=C3C(=O)N2C1)OC)O)OC;
Properties
Chemical formula	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] Tomaymycin is produced by the bacterium Streptomyces achromogenes.^[2]

References

^ ^a ^b ^c "Tomaymycin". Pubchem.ncbi.NLM.nih.gov.
^ ^a ^b 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. Bibcode:2009ApEnM..75.2958L. doi:10.1128/AEM.02325-08. PMC 2681672. PMID 19270147.
^ 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.

Szeinbach, Sheryl Lynn (1983). 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). 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. S2CID 213969939.

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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
CAS Number	35050-55-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:157681 CHEBI:167318
ChEMBL	ChEMBL580013
ChemSpider	13076951
PubChem CID	12444380
InChI InChI=1S/C16H20N2O4/c1-4-9-5-12-15(22-3)17-11-7-13(19)14(21-2)6-10(11)16(20)18(12)8-9/h4,6-7,12,15,17,19H,5,8H2,1-3H3/b9-4-/t12-,15+/m0/s1 Key: UQVNRKBFAXNOGA-OHLDGCSVSA-N
SMILES C/C=C\1/C[C@H]2[C@H](NC3=CC(=C(C=C3C(=O)N2C1)OC)O)OC
Properties
Chemical formula	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