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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 ?-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.

SUBMITTER: Cai X

PROVIDER: S-EPMC4059221 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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

Cai Xiao X Ng Kevin K Panesar Harmanpreet H Moon Seong-Jin SJ Paredes Maria M Ishida Keishi K Hertweck Christian C Minehan Thomas G TG

Organic letters 20140513 11

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 gilvocarci ...[more]

PMID: 24824354

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