Issue 44, 2014

Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Abstract

The unusual sugars, α-aculosides, which appear in certain antibiotics and have an α,β-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine residues. A coumarin derivative possessing α-aculoside as a Michael acceptor effectively and irreversibly operated as a fluorescent probe in cells. Furthermore, α-aculosides exhibited cytotoxic activity against several cancer cell lines.

Graphical abstract: Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Supplementary files

Article information

Article type
Communication
Submitted
03 Sep 2014
Accepted
18 Sep 2014
First published
18 Sep 2014

Org. Biomol. Chem., 2014,12, 8832-8835

Author version available

Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

H. Ikeda, E. Kaneko, S. Okuzawa, D. Takahashi and K. Toshima, Org. Biomol. Chem., 2014, 12, 8832 DOI: 10.1039/C4OB01877J

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