185741-59-7

Upstream product

• 150965-65-4 2,3-O-Isopropylidene-5-O-trifluoromethanesulfonyl-L-rhamnono-1,4-lactone 
• 185741-56-4 (3aR,6S,6aR)-6-((R)-1-Azido-ethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 
• 185741-58-6 (4R,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide 
• 72127-46-9 6-deoxy-2,3-O-isopropylidene-L-talono-1,4-lactone 
• 214897-78-6 (4S,5R)-5-((1S,2R)-2-Azido-1-hydroxy-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbonitrile 

Relevant academic research and scientific papers

5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-L- rhamnosidase: 5-epi-Deoxymannojirimycin is not a potent inhibitor of an α- D-mannosidase

Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an α-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an α-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L- rhamnose which are recognised by enzymes that synthesise or process L- rhamnose may inhibit either the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-5 epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the 4H3 conformation of the relevant glycopyranosyl cation intermediate.

Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids

L-Deoxyrhamnojirimycin 1 does not inhibit naringinase significantly but 5-epi-L-deoxyrhamnojirimycin 2 is a potent inhibitor. Conversely, α-C-glycosides of 1 are good inhibitors of L-rhamnosidase whereas those of 2 are not. Intermediate azabicyclic lactones are likely to be of use for the incorporation of a number of trihydrocypipecolic acids into peptide libraries.