Total synthesis of the antitumor natural product polycarcin V and evaluation of its DNA binding profile.
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.
Department of Chemistry and Biochemistry, California State University, Northridge , 18111 Nordhoff Street, Northridge, California 91330, United States.
Xiao
X
Cai
Kevin
K
Ng
Harmanpreet
H
Panesar
Seong-Jin
SJ
Moon
Maria
M
Paredes
Keishi
K
Ishida
Christian
C
Hertweck
Thomas G
TG
Minehan
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D045744:Cell Line, Tumor; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D006801:Humans; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001688:Biological Products; D003374:Coumarins; D006027:Glycosides; D009284:Naphthols; C534478:polycarcin V; C031781:gilvocarcin V; D004247:DNA