Shane Rountree

2-Acetamido-1,4-imino-1,2,4-trideoxy-D-ribitol (DRBNAc) and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L- and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of alpha- or beta-hexosaminidases or any other glycosidase. (C) 2010 Academie des sciences. Published by...

Sandhoff and Tay-Sachs disease are autosomal recessive GM2 gangliosidoses where a deficiency of lysosomal beta-hexosaminidase results in storage of glycoconjugates. Imino sugar (2-acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol) inhibition of beta-hexosaminidase in murine RAW264.7 macrophage-like cells led to lysosomal storage of glycoconjugates th...

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Illuminating glucosidases: The shown photoaffinity probe for endoplasmic reticulum (ER) α-glucosidases was found to be a highly potent inhibitor of α-glucosidase I in vitro and equally effective at inhibiting cellular ER glucosidases, as determined by a free oligosaccharide (FOS) analysis. The N-alkylated deoxynojirimycin compound, N-(6′-(4′′-azido...

N-Acetylhexosaminidases are of considerable importance in mammals and are involved in various significant biological processes. In humans, deficiencies of these enzymes in the lysosome, resulting from inherited genetic defects, cause the glycolipid storage disorders Tay-Sachs and Sandhoff diseases. One promising therapy for these diseases involves...

The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.

The synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-benzyl LABNAc are potent non-competitive inhibitors of d-hexosaminidase, whereas N-benzyl DABNA...

The solid-state conformation of the title compound, C14H20N2O3·0.33H2O, a potent hexosaminidase inhibitor, prepared from d-lyxonolactone, has been established by X-ray crystallography. The asymmetric unit contains three mol­ecules, which have very similar conformations, together with a mol­ecule of water.

The solid-state conformation of the title compound, C14H20N2O3·0.33H2O, a potent hexosaminidase inhibitor, prepared from d-lyxonolactone, has been established by X-ray crystallography. The asymmetric unit contains three mol­ecules, which have very similar conformations, together with a mol­ecule of water.

The molecular structure of 2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-ribitol was investigated. The relative configuration of the stereocentres in a potential hexosaminidase inhibitor, the compound, prepared from D-lyxonolactone, had been established using X-ray crystallographic techniques. The compound was crystallized by cooling a warm solut...