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

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.