Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase,an α-l-rhamnosidase competitively |
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Authors: | Thomas B Mercer Sarah F Jenkinson Barbara Bartholomew Robert J Nash Saori Miyauchi Atsushi Kato George WJ Fleet |
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Institution: | 1. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;2. Phytoquest Limited, IBERS, Plas Gogerddan, Aberystwyth SY23 3EB, Ceredigion, Wales, UK;3. Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan |
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Abstract: | Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-l-lyxitol (LIL). DIL showed potent Ki = 0.13 μM]—and LIL showed weak Ki = 113 μM]—competitive inhibition of α-d-galactosidase. Both enantiomers N-benzyl-DIL Ki = 64 μM] and N-benzyl-LIL Ki = 13 μM] were moderate competitive inhibitors of naringinase, an α-l-rhamnosidase. |
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