Kinamycin

Kinamycin is a group of bacterial polyketide secondary metabolites containing a diazo group. Kinamycins are known for their cytotoxicity and are considered of interest for potential use in anti-cancer therapies.^[1][2]

Synthesis

In 2006 and 2007 the means to totally and enantioselectively synthesize Kinamycin C, F, and J were discovered.^[3][4] In 2010 a method was found to allow easier synthesis of these compounds in fewer steps, making research into their properties more feasible.^[5]

References

1. Ballard, T. E.; Melander, C. (2008). "Kinamycin-mediated DNA cleavage under biomimetic conditions". Tetrahedron Letters 49 (19): 3157. doi:10.1016/j.tetlet.2008.03.019.
2. O'Hara, K. A.; Wu, X.; Patel, D.; Liang, H.; Yalowich, J. C.; Chen, N.; Goodfellow, V.; Adedayo, O.; Dmitrienko, G. I.; Hasinoff, B. B. (2007). "Mechanism of the cytotoxicity of the diazoparaquinone antitumor antibiotic kinamycin F". Free Radical Biology and Medicine 43 (8): 1132–1144. doi:10.1016/j.freeradbiomed.2007.07.005. PMC 2753228. PMID 17854709.
3. Lei, X.; Porco Ja, J. (2006). "Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1". Journal of the American Chemical Society 128 (46): 14790–14791. doi:10.1021/ja066621v. PMID 17105273.
4. Nicolaou, K. C.; Li, H.; Nold, A. L.; Pappo, D.; Lenzen, A. (2007). "Total Synthesis of Kinamycins C, F, and J". Journal of the American Chemical Society 129 (34): 10356–7. doi:10.1021/ja074297d. PMID 17676854.
5. Woo, C. M.; Lu, L.; Gholap, S. L.; Smith, D. R.; Herzon, S. B. (2010). "Development of a Convergent Entry to the Diazofluorene Antitumor Antibiotics: Enantioselective Synthesis of Kinamycin F". Journal of the American Chemical Society 132 (8): 2540–1. doi:10.1021/ja910769j. PMID 20141138.

External links

• EMBL-EBI listing—includes links to structural formula and other properties of group members
• Description of Porco(2006) and Nicolaou(2007) synthesis on University of Pittsburgh site