Total synthesis of the antitumor natural product polycarcin V and evaluation of its DNA binding profile.

Abstract

The convergent total synthesis of polycarcin V, a gilvocarcin-type natural product that shows significant cytotoxicity with selectivity for nonsmall-cell lung cancer, breast cancer, and melanoma cells, has been achieved in 13 steps from 7, 8, and 22; the sequence features a stereoselective α-C-glycosylation reaction for the union of protected carbohydrate 7 and naphthol 8. The association constant for the binding of polycarcin V to duplex DNA is similar to that previously reported for gilvocarcin V.

• Authors: Xiao Cai, Kevin Ng, Harmanpreet Panesar, Seong-Jin Moon, Maria Paredes, Keishi Ishida, Christian Hertweck, Thomas G Minehan
• Journal: Organic letters (Org Lett) Vol. 16 Issue 11 Pg. 2962-5 (Jun 06 2014) ISSN: 1523-7052 [Electronic] United States
• PMID: 24824354 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Aminoglycosides
• Anti-Bacterial Agents
• Antineoplastic Agents
• Biological Products
• Coumarins
• Glycosides
• Naphthols
• polycarcin V
• gilvocarcin V
• DNA

Topics

• Aminoglycosides
• Anti-Bacterial Agents (chemical synthesis, chemistry)
• Antineoplastic Agents (chemical synthesis, chemistry)
• Biological Products (chemical synthesis, chemistry)
• Cell Line, Tumor
• Coumarins (chemical synthesis, chemistry)
• DNA (chemistry)
• Glycosides (chemical synthesis, chemistry)
• Glycosylation
• Humans
• Molecular Structure
• Naphthols (chemistry)