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

J.P. Shilvock; J.R. Wheatley; B. Davis; R.J. Nash; R.C. Griffiths; M.G.K. Jones; M. Müller; S. Crook; D.J. Watkin; C. Smith; G.S. Besra; P.J. Brennan; G.W.J. Fleet

doi:10.1016/0040-4039(96)01958-2

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

Journal article

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

J.P. Shilvock, J.R. Wheatley, B. Davis, R.J. Nash, R.C. Griffiths, M.G.K. Jones, M. Müller, S. Crook, D.J. Watkin, C. Smith, …

Tetrahedron Letters, Vol.37(47), pp.8569-8572

1996

DOI: 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.

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Title: Inhibition of naringinase (L-rhamnosidase) by piperidine analogues of L-rhamnose: Scaffolds for libraries incorporating trihydroxypipecolic acids
Authors/Creators: J.P. Shilvock (Author/Creator) - University of Oxford
J.R. Wheatley (Author/Creator) - University of Oxford
B. Davis (Author/Creator) - University of Oxford
R.J. Nash (Author/Creator) - Aberystwyth University
R.C. Griffiths (Author/Creator) - Aberystwyth University
M.G.K. Jones (Author/Creator)
M. Müller (Author/Creator) - Chemical Crystallography Laboratory, 9, Parks Road, Oxford OX1 3QU, UK
S. Crook (Author/Creator) - Chemical Crystallography Laboratory, 9, Parks Road, Oxford OX1 3QU, UK
D.J. Watkin (Author/Creator) - Chemical Crystallography Laboratory, 9, Parks Road, Oxford OX1 3QU, UK
C. Smith (Author/Creator)
G.S. Besra (Author/Creator)
P.J. Brennan (Author/Creator) - Colorado State University
G.W.J. Fleet (Author/Creator) - University of Oxford
Publication Details: Tetrahedron Letters, Vol.37(47), pp.8569-8572
Publisher: Elsevier BV
Identifiers: 991005542631507891
Copyright: © 1996 Elsevier Ltd.
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

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Collaboration types: Industry collaboration; Domestic collaboration; International collaboration
Citation topics: 2 Chemistry; 2.1 Synthesis; 2.1.1145 Iminosugar Synthesis
Web Of Science research areas: Chemistry, Organic
ESI research areas: Chemistry