Kinamycin

Kinamycins are 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]

Chemical structure of kinamycin A

Synthesis

In 2006 and 2007 the means to totally and enantioselectively synthesize kinamycins 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

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.
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.
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.
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.
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 kinamycin (CHEBI:48207)
Description of Porco(2006) and Nicolaou(2007) synthesis on University of Pittsburgh site

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[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.