Bactobolin

Bactobolin is a cytotoxic, polyketide-peptide and antitumor antibiotic with the molecular formula C14H20Cl2N2O6.[2][3][4][5] Bactobolin was discovered in 1979.[6]

Bactobolin
Names
IUPAC name
(2S)-N-[(3S,4R,4aR,5R,6R)-3-(Dichloromethyl)-5,6,8-trihydroxy-3-methyl-1-oxo-4a,5,6,7-tetrahydro-4H-isochromen-4-yl]-2-aminopropanamide[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C14H20Cl2N2O6/c1-4(17)11(22)18-10-8-7(5(19)3-6(20)9(8)21)12(23)24-14(10,2)13(15)16/h4,6,8-10,13,19-21H,3,17H2,1-2H3,(H,18,22)/t4-,6+,8-,9-,10+,14-/m0/s1
    Key: RBCHRRIVFAIGFI-RGBMRXMBSA-N
  • C[C@@H](C(=O)N[C@@H]1[C@@H]2[C@H]([C@@H](CC(=C2C(=O)O[C@]1(C)C(Cl)Cl)O)O)O)N
Properties
C14H20Cl2N2O6
Molar mass 383.22 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

References

  1. "Bactobolin". pubchem.ncbi.nlm.nih.gov.
  2. Greenberg, E. Peter; Chandler, Josephine R.; Seyedsayamdost, Mohammad R. (27 March 2020). "The Chemistry and Biology of Bactobolin: A 10-Year Collaboration with Natural Product Chemist Extraordinaire Jon Clardy". Journal of Natural Products. 83 (3): 738–743. doi:10.1021/acs.jnatprod.9b01237. hdl:1808/32425.
  3. Weinreb, Steven M. (1995). "Total synthesis of the microbial antitumor antibiotics actinobolin and bactobolin". Studies in Natural Products Chemistry. 16: 3–25. doi:10.1016/S1572-5995(06)80051-7.
  4. Munakata, Tomohiko; Ikeda, Yoshifumi; Matsuki, Hideo; Isagai, Katsuyoshi (May 1983). "Cultural Conditions and Strain Improvement for Production of Bactobolin". Agricultural and Biological Chemistry. 47 (5): 929–934. doi:10.1080/00021369.1983.10865772.
  5. Franco, Carlos M.; Belda, Beatriz Vázquez (2 December 2020). Natural Compounds as Antimicrobial Agents. MDPI. p. 134. ISBN 978-3-03936-048-2.
  6. Reinhoudt, D. N.; Connors, T. A.; Pinedo, H. M.; Poll, K. W. van de (6 December 2012). Structure-Activity Relationships of Anti-Tumour Agents. Springer Science & Business Media. p. 270. ISBN 978-94-009-6798-4.

Further reading

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