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

B. Davis; A.A. Bell; R.J. Nash; A.A. Watson; R.C. Griffiths; M.G.K. Jones; C. Smith; G.W.J. Fleet

doi:10.1016/0040-4039(96)01957-0

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

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

B. Davis, A.A. Bell, R.J. Nash, A.A. Watson, R.C. Griffiths, M.G.K. Jones, C. Smith and G.W.J. Fleet

Tetrahedron Letters, Vol.37(47), pp.8565-8568

1996

DOI: 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).

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Title: L-(+)-swainsonine and other pyrrolidine inhibitors of naringinase: Through an enzymic looking glass from D-mannosidase to L-rhamnosidase?
Authors/Creators: B. Davis (Author/Creator) - University of Oxford
A.A. Bell (Author/Creator) - University of Oxford
R.J. Nash (Author/Creator) - Aberystwyth University
A.A. Watson (Author/Creator) - Aberystwyth University
R.C. Griffiths (Author/Creator) - Aberystwyth University
M.G.K. Jones (Author/Creator)
C. Smith (Author/Creator)
G.W.J. Fleet (Author/Creator) - University of Oxford
Publication Details: Tetrahedron Letters, Vol.37(47), pp.8565-8568
Publisher: Elsevier BV
Identifiers: 991005542737507891
Murdoch Affiliation: Murdoch University
Language: English
Resource Type: Journal article

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