24923-78-2Relevant academic research and scientific papers
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA
Mendgen, Thomas,Scholz, Therese,Klein, Christian D.
supporting information; experimental part, p. 5757 - 5762 (2010/12/24)
The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity relationships of various derivatives. The inhibition of MurA can be related to antibacterial activity, and MurA is probably one of the relevant molecular targets of the tulipaline derivatives. MurA inhibition by this class of compounds depends on the presence of the substrate UNAG, which indicates non-covalent suicide inhibition as observed previously for cnicin. With respect to selectivity, however, the reactivity against arbitrary sulfhydryl groups, such as in glutathione, could not yet be sufficiently separated from MurA inhibition in the present dataset.
Allergenic α-Methylene-γ-lactones. General Method for the Preparation of β-Acetoxy- and β-Hydroxy-α-methylene-γ-butyrolactones from Sulfoxides. Application to the Synthesis of a Tuliposide B Derivative
Corbet, Jean-Pierre,Benezra Claude
, p. 1141 - 1147 (2007/10/02)
A general synthesis of β-hydroxy-α-methylene-γ-butyrolactones , which is based on the sulfoxide-sulfenate rearrangement, is presented.Several β-acetoxy-α-methylene-γ-butyrolactones have been prepared and transformed into the β-hydroxy-derivatives through base hydrolysis.This synthesis has been applied to the first preparation of (tetraacetoxybenzyl)tuliposide B (22).
