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

Shilvock, J.P., Wheatley, J.R., Davis, B., Nash, R.J., Griffiths, R.C., Jones, M.G.K.ORCID: 0000-0001-5002-0227, Müller, M., Crook, S., Watkin, D.J., Smith, C., Besra, G.S., Brennan, P.J. and Fleet, G.W.J. (1996) Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids. Tetrahedron Letters, 37 (47). pp. 8569-8572.

Link to Published Version: https://doi.org/10.1016/0040-4039(96)01958-2
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Abstract

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 trihydroxypipecolic acids into peptide libraries.

Both 2 and 3 are potent inhibitors of naringinase (L-rhamnosidase); neither 1 nor 4 cause any significant inhibition.

Item Type: Journal Article
Publisher: Elsevier BV
Copyright: © 1996 Elsevier Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/49575
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