219992-19-5Relevant academic research and scientific papers
Enantioselective synthesis of α-hydroxylated enterolactone and analogs
Sefkow, Michael,Kelling, Alexandra,Schilde, Uwe
, p. 5101 - 5104 (2007/10/03)
A short and general synthesis of enantiomerically pure α-hydroxylated lactone lignans starting from commercially available iPr malate is presented. Key reactions are two stereoselective alkylations of malic acid derivatives. Some enhancements of the alkylation of malic acid esters and a general extension of the alkylation of dioxolanones is reported. Proof of the stereochemical outcome of the alkylation reactions is provided by X-ray diffraction analysis of α-hydroxy-α,β-dibenzyl-γ-butyrolactone, the first crystal structure of an enantiomerically pure α-hydroxylated lactone lignan.
Hydrogen bonding and attenuation of the rate of enzymic catalysis
Li, Zhi-Hong,Bulychev, Alexey,Kotra, Lakshmi P.,Massova, Irina,Mobashery, Shahriar
, p. 13003 - 13007 (2007/10/03)
Hydrogen bonds between a small molecule and an enzyme can potentially contribute significantly to the stability of the complex. Such electrostatic interactions can also lower energy barriers for reactions by solvation of high-energy species. A novel type
