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// Workers AI · dad joke modeWhat did Legonmycin say? It's a block-buster antibiotic.

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChemSpider
  • 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
  • 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
A: C13H20N2O3
B: C14H22N2O3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

[edit]
  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.
  2. Pius Amihere Eduku (August 6, 2015). "New cancer fighting agent named after Legon". Citifmonline. Retrieved August 7, 2015.
  3. Betty Kankam-Boadu (August 8, 2015). "New cancer fighting agent named after University of Ghana". Pulse.com. Retrieved August 7, 2015.
  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.