Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids
Shilvock JP., Wheatley JR., Davis B., Nash RJ., Griffiths RC., Jones MG., Müller M., Crook S., Watkin DJ., Smith C., Besra GS., Brennan PJ., Fleet GWJ.
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.