Legonmycin

Legonmycin
	Legonmycin A (top) and legonmycin B
Names
	IUPAC names A: N-(8-Hydroxy-2-methyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl)-3-methylbutanamide ; B: N-(8-Hydroxy-2-methyl-1-oxo-6,7-dihydro-5H-pyrrolizin-3-yl)-4-methylpentanamide
Identifiers
CAS Number	A: 1802522-27-5; B: 1802522-28-6;
3D model (JSmol)	A: Interactive image; B: Interactive image;
ChemSpider	A: 40257825;
PubChem CID	A: 139585189; B: 156583135;
	InChI A: InChI=1S/C13H20N2O3/c1-8(2)7-10(16)14-12-9(3)11(17)13(18)5-4-6-15(12)13/h8,18H,4-7H2,1-3H3,(H,14,16) Key: PLSCDSCQUZWYJL-UHFFFAOYSA-N; B: InChI=1S/C14H22N2O3/c1-9(2)5-6-11(17)15-13-10(3)12(18)14(19)7-4-8-16(13)14/h9,19H,4-8H2,1-3H3,(H,15,17) Key: STVITZBETCSTPL-UHFFFAOYSA-N;
	SMILES A: CC1=C(N2CCCC2(C1=O)O)NC(=O)CC(C)C; B: CC1=C(N2CCCC2(C1=O)O)NC(=O)CCC(C)C;
Properties
Chemical formula	A: C13H20N2O3 ; B: C14H22N2O3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Legonmycins are a group of chemical compounds that belong to the pyrrolizidine family of naturally occurring alkaloids. Discovered by a joint team of researchers from University of Ghana, University of Aberdeen, and Wuhan University, the compounds were isolated from Streptomyces microorganisms in Legon, a suburb of Accra, Ghana.^[1]^[2]^[3]^[4] Laboratory syntheses of legonmycin A and legonmycin B have been reported.^[5]

References

↑ Huang, Sheng; Tabudravu, Jioji; Elsayed, Somayah S.; Travert, Jeanne; Peace, Doe; Tong, Ming Him; Kyeremeh, Kwaku; Kelly, Sharon M.; Trembleau, Laurent; Ebel, Rainer; Jaspars, Marcel; Yu, Yi; Deng, Hai (2015). "Discovery of a Single Monooxygenase that Catalyzes Carbamate Formation and Ring Contraction in the Biosynthesis of the Legonmycins". Angewandte Chemie International Edition. 54 (43): 12697–12701. doi:10.1002/anie.201502902. PMID 26206556.
↑ Pius Amihere Eduku (August 6, 2015). "New cancer fighting agent named after Legon". Citifmonline. Retrieved August 7, 2015.
↑ Betty Kankam-Boadu (August 8, 2015). "New cancer fighting agent named after University of Ghana". Pulse.com. Retrieved August 7, 2015.
↑ "University of Ghana discovers Cancer fighting agents". Ghana News Agency. August 5, 2015. Retrieved August 7, 2015.
↑ Lewis WJM; Shaw, D. M.; Robertson, J. (2021). "Synthesis of legonmycins a and B, C(7a)-hydroxylated bacterial pyrrolizidines". Beilstein Journal of Organic Chemistry. 17: 334–342. doi:10.3762/bjoc.17.31. PMC 7871033. PMID 33828615.

[1] Huang, Sheng; Tabudravu, Jioji; Elsayed, Somayah S.; Travert, Jeanne; Peace, Doe; Tong, Ming Him; Kyeremeh, Kwaku; Kelly, Sharon M.; Trembleau, Laurent; Ebel, Rainer; Jaspars, Marcel; Yu, Yi; Deng, Hai (2015). "Discovery of a Single Monooxygenase that Catalyzes Carbamate Formation and Ring Contraction in the Biosynthesis of the Legonmycins". Angewandte Chemie International Edition. 54 (43): 12697–12701. doi:10.1002/anie.201502902. PMID 26206556.

[city-2] Pius Amihere Eduku (August 6, 2015). "New cancer fighting agent named after Legon". Citifmonline. Retrieved August 7, 2015.

[PULSE-3] Betty Kankam-Boadu (August 8, 2015). "New cancer fighting agent named after University of Ghana". Pulse.com. Retrieved August 7, 2015.

[gna-4] "University of Ghana discovers Cancer fighting agents". Ghana News Agency. August 5, 2015. Retrieved August 7, 2015.

[5] Lewis WJM; Shaw, D. M.; Robertson, J. (2021). "Synthesis of legonmycins a and B, C(7a)-hydroxylated bacterial pyrrolizidines". Beilstein Journal of Organic Chemistry. 17: 334–342. doi:10.3762/bjoc.17.31. PMC 7871033. PMID 33828615.

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