Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively

Thomas B. Mercer, Sarah F. Jenkinson, Barbara Bartholomew, Robert J. Nash, Saori Miyauchi, Atsushi Kato, George W. J. Fleet

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42 Citations (SciVal)

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 [K(i) = 0.13 mu M]-and LIL showed weak [K(i) = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K(i) = 64 mu M] and N-benzyl-LIL [K(i) = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase.
Original languageEnglish
Pages (from-to)2368-2373
Number of pages6
JournalTetrahedron: Asymmetry
Volume20
Issue number20
DOIs
Publication statusPublished - 20 Oct 2009

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