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Characteristic Stereostructures and Regioselectivity of Biogenic Pathway of FPTase Inhibition Materials Isolated from Artemisia sylvatica  

Kwon, Byung-Mok (Korea research Institute of Bioscience and Biotechnology)
Sung, Nack-Do (Divition of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Publication Information
Applied Biological Chemistry / v.45, no.4, 2002 , pp. 223-227 More about this Journal
Abstract
Characteristic stereostructures of farnesyl protein transferase (FPTase) inhibition materials isolated from Artemisia sylvatica and regioselectivity of biogenic Diels-Alder reactions between dehydromatricarin molecules A and B were examined quantitatively. Results revealed that the major reaction of frontier molecular orbital (FMO) interaction proceeds through charge-control reaction between LUMO of A16, dienophile and HOMO of B1, diene, and the isolated 8-acetylarteminolide and artanomaloide were minor products. FPTase inhibition activity and hydrophobicity of 8-acetylarteminolide were $pI_{50}=3.75$ and logP=2.62, respectively. FPTase inhibition activity of 8-acetylarteminolide was higher than those of artanomaloide and dehydromatricarin.
Keywords
FPTase inhibition materials; Artemisia sylvatica Max.; biogenic Diels-Alder reaction; frontier molecular orbital (FMO) interaction; regioselectivity;
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