Glionitrin A

Glionitrin A
Names
	IUPAC name (3R,10aR)-3-(hydroxymethyl)-2-methyl-7-nitro-2,3-dihydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Identifiers
CAS Number	1116153-15-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	28286042;
PubChem CID	42611028;
	InChI InChI=1S/C13H11N3O5S2/c1-14-10(18)12-5-7-2-3-8(16(20)21)4-9(7)15(12)11(19)13(14,6-17)23-22-12/h2-4,17H,5-6H2,1H3 Key: VRFJINVAZRAFHH-UHFFFAOYSA-N;
	SMILES CN1C(=O)C23CC4=C(N2C(=O)C1(SS3)CO)C=C(C=C4)[N+](=O)[O-];
Properties
Chemical formula	C13H11N3O5S2
Molar mass	353.37 g·mol−1
Appearance	Yellow powder
Melting point	181-182 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glionitrin A is an antibiotic-anticancer compound made by microbes found in an abandoned mine.^[1] The total synthesis of (−)-glionitrin A was reported by Daniel Strand and co-workers in 2021.^[2]

References

^ Park, H. B.; Kwon, H. C.; Lee, C. H.; Yang, H. O. (February 2009). "Glionitrin A, an antibiotic-antitumor metabolite derived from competitive interaction between abandoned mine microbes". J. Nat. Prod. 72 (2): 248–52. doi:10.1021/np800606e. PMID 19159274.
^ Koning, N.R.; Sundin, A.P.; Strand, D. (22 November 2021). "Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines". J. Am. Chem. Soc. 143 (50): 21218–21222. doi:10.1021/jacs.1c10364. PMC 8704193. PMID 34808045.

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[1] Park, H. B.; Kwon, H. C.; Lee, C. H.; Yang, H. O. (February 2009). "Glionitrin A, an antibiotic-antitumor metabolite derived from competitive interaction between abandoned mine microbes". J. Nat. Prod. 72 (2): 248–52. doi:10.1021/np800606e. PMID 19159274.

[2] Koning, N.R.; Sundin, A.P.; Strand, D. (22 November 2021). "Total Synthesis of (−)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines". J. Am. Chem. Soc. 143 (50): 21218–21222. doi:10.1021/jacs.1c10364. PMC 8704193. PMID 34808045.

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