596828-45-4

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 900865-45-4 Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 596828-50-1 (R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-13-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-tridecan-1-ol 
• 596828-49-8 (E)-(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-undec-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-13-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-tridec-5-en-3-yn-1-ol 
• 596828-48-7 Acetic acid (S)-2-[(2R,5R,2'R,5'R)-5'-((R)-1-acetoxy-undec-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester 

Relevant academic research and scientific papers

Function of the alkyl side chains of Δlac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase)

We synthesized a series of Δlac-acetogenins in which the two alkyl side chains were systematically modified, and examined their inhibitory effect on bovine heart mitochondrial complex I (NADH-ubiquinone oxidoreductase). The results revealed that the physicochemical properties of the side chains, such as the balance of hydrophobicity and the width (or bulkiness) of the chains, are important structural factors for a potent inhibitory effect of amphiphilic Δlac-acetogenins. This is probably because such properties decide the precise location of the hydrophilic bis-THF ring moiety in the enzyme embedded in the inner mitochondrial membrane.

Synthesis and inhibitory activity of ubiquinone-acetogenin hybrid inhibitor with bovine mitochondrial complex I

To elucidate the inhibitory action of acetogenins, the most potent inhibitors of mitochondrial complex I, we synthesized an acetogenin analogue which possesses a ubiquinone ring (i.e., the physiological substrate of complex I) in place of the α,β-unsatura