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L-(+)-swainsonine and other pyrrolidine inhibitors of naringinase: Through an enzymic looking glass from D-mannosidase to L-rhamnosidase?

Davis, B., Bell, A.A., Nash, R.J., Watson, A.A., Griffiths, R.C., Jones, M.G.K.ORCID: 0000-0001-5002-0227, Smith, C. and Fleet, G.W.J. (1996) L-(+)-swainsonine and other pyrrolidine inhibitors of naringinase: Through an enzymic looking glass from D-mannosidase to L-rhamnosidase? Tetrahedron Letters, 37 (47). pp. 8565-8568.

Link to Published Version: https://doi.org/10.1016/0040-4039(96)01957-0
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Abstract

The synthesis and inhibitory properties towards naringinase (L-rhamnosidase) of L-(+)-swainsonine and of a number of more highly oxygenated analogues, and of some monocyclic equivalents, are reported. L-(+)-swainsonine and 1,4,6-trideoxy-1,4-imino-L-mannitol are powerful and specific inhibitors of naringinase.

The synthesis of unnatural L-(+)-swainsonine 1, the enantiomer of the powerful D-mannosidase inhibitor, and of more highly oxygenated derivatives thereof is reported. Both 1 and the pyrrolidine 2 are potent inhibitors of naringinase (L-rhamnosidase).

Item Type: Journal Article
Publisher: Elsevier BV
URI: http://researchrepository.murdoch.edu.au/id/eprint/49577
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