Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 20, Pages 6979-6987Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob05932g
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Funding
- European Union [LSHC-CT-2005-518417]
- MICIIN-Spain [SAF2010-17935-FEDER]
- Xunta de Galicia [08CSA052383PR, 2006/15]
- Associazione Italiana per la Ricerca sul Cancro Funding Source: Custom
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The purported structures of the peyssonenynes A and B isolated from Peyssonnelia caulifera, and considered to be geometric isomers at the acetoxyenediyne moiety, have been synthesized. The E and Z geometries of the synthetic compounds were secured by the magnitude of the (3)J(H9-C7) values measured using the EXSIDE band-variant of the gradient HSQC pulse sequence and by the chemical shifts of C-6. Comparison of the NMR data of the synthetic and natural products revealed that only those of the Z isomers matched, which correspond to peyssonenyne A. Using HPLC analysis it was found that peyssonenyne B must correspond to the sn-2 positional isomer of the Z sn-1/3 counterpart. The four synthetic sn-1/3 diastereomers are roughly equipotent as DNMT1 inhibitors when evaluated on a radioactive methyl transfer enzymatic assay after immunoprecipitation from K562 human leukemia cells with anti-DNMT1 antibody.
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