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Kee, Jung-Min
Bioorganic and Chembio Lab
Research Interests
  • Chemical biology, organic synthesis, peptide chemistry, synthetic protein chemistry

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Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities

Cited 15 times inthomson ciCited 15 times inthomson ci
Title
Gateway synthesis of daphnane congeners and their protein kinase C affinities and cell-growth activities
Author
Wender, Paul A.Buschmann, NicoleCardin, Nate B.Jones, Lisa R.Kan, CindyKee, Jung-MinKowalski, John A.Longcore, Kate E.
Issue Date
2011-08
Publisher
NATURE PUBLISHING GROUP
Citation
NATURE CHEMISTRY, v.3, no.8, pp.615 - 618
Abstract
The daphnane diterpene orthoesters constitute a structurally fascinating family of natural products that exhibit a remarkable range of potent biological activities. Although partial activity information is available for some natural daphnanes, little information exists for non-natural congeners or on how changes in structure affect mode of action, function, potency or selectivity. A gateway strategy designed to provide general synthetic access to natural and non-natural daphnanes is described and utilized in the synthesis of two novel members of this class. In this study, a commercially available tartrate derivative was elaborated through a key late-stage diversification intermediate into B-ring yuanhuapin analogues to initiate exploration of the structure-function relationships of this class. Protein kinase C was identified as a cellular target for these agents, and their activity against human lung and leukaemia cell lines was evaluated. The natural product and a novel non-natural analogue exhibited significant potency, but the epimeric epoxide was essentially inactive.
URI
https://scholarworks.unist.ac.kr/handle/201301/13399
URL
http://www.nature.com/nchem/journal/v3/n8/full/nchem.1074.html
DOI
10.1038/nchem.1074
ISSN
1755-4330
Appears in Collections:
CHM_Journal Papers
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