A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the...

Two water-soluble glycoasparagine storage products were isolated from the liver of a patient with inherited deficiency of lysosomal N-aspartyl-beta-glucosaminidase (aspartylglycosaminuria). The compounds were characterized using gas chromatographic-mass spectrometric analyses of intact and specifically degraded derivatives. The storage compounds were identified as 2-acetamido-1-N-(4'-L-aspartyl...

β-acetamido ketones were synthesized in excellent yields through one-pot condensation reaction of aldehydes, acetophenones, acetyl chloride, and acetonitrile in the presence of boric acid as a solid heterogeneous catalyst at room temperature. It is the first successful report of boric acid that has been used as solid acid catalyst for the preparation of β-acetamido ketones. The remarkable advan...

A large scale isolation of a disaccharide from a dialyzable fraction cf Micrococcus Zysodeikticus cell wall is described. This fraction was obtained by degradation of isolated walls with egg white lysozyme. After purification by chromatography on charcoal-Celite 2nd Dowex 1, the compound was characterized by a crystalline heptaacetyl methyl ester. Comparison with synthetic 0-2-acetamido-2-deoxy...

The functionalisation of oligodeoxynucleotides and oligoribonucleotides by incorporation of 2'-amido-2'-deoxyribonucleosides, possibly containing a reporter group via the 2'-amido bond, was examined. Therefore 2'-acetamido-ribonucleosides containing a small methyl group at the 2'-amido bond were synthesized as model compounds. In order to evaluate the influence of this 2'-modification on the hy...

A large scale isolation of a disaccharide from a dialyzable fraction cf Micrococcus Zysodeikticus cell wall is described. This fraction was obtained by degradation of isolated walls with egg white lysozyme. After purification by chromatography on charcoal-Celite 2nd Dowex 1, the compound was characterized by a crystalline heptaacetyl methyl ester. Comparison with synthetic 0-2-acetamido-2-deoxy...

change is the greatest. Indeed, in that orientation the C3 hydroxyl group is directed toward the acetamido group (rather than away from it), and the intramolecular interactions stabilizing such an orientation would become more significant as the solvent polarity is lowered. Evidence supporting such a hypothesis, independent of the present theoretical model, is presented in Table 11, which displ...

It has been shown that the acetamido methyl protons of N-acetyl-D-glucosamine undergo a chemical shift to higher fields in their proton magnetic resonance spectrum when the inhibitor is bound to lysozyme. The observed chemical shift in the presence of the enzyme is different for the CP and /3-anomeric forms of Z-acetamido-Z-deoxy-D-glucopyranose indicating either a difference in the afhnity of ...

Two distinct 2-acetamido-2-deoxy-alpha-D-galactosidases have been separated from filtrates of cultured Clostridium perfringens by electrophoresis in 6.5% poly(acrylamide) gels. One of the enzymes had a mobility of 0.32--0.36 (relative to Bromophenol Blue) and was identified as the exoglycosidase, 2-acetamido-2-deoxy-alpha-D-galactosidase. It appears to be the same enzyme as that reported in 197...