148968-89-2Relevant academic research and scientific papers
Synthesis and high-throughput screening of N-acetyl-β-hexosaminidase inhibitor libraries targeting osteoarthritis
Liu, Junjie,Numa, Mehdi M. D.,Liu, Haitian,Huang, Shi-Jung,Sears, Pamela,Shikhman, Alexander R.,Wong, Chi-Huey
, p. 6273 - 6283 (2007/10/03)
C1 Nitrogen iminocyclitols are potent inhibitors of N-acetyl-β- hexosaminidases. Given hexosaminidases' important roles in osteoarthritis, we developed two straightforward and efficient syntheses of C1 nitrogen iminocyclitols from two readily available starting materials, D-mannosamine hydrochloride and the microbial oxidation product of fructose. A diversity-oriented synthetic strategy was then performed by coupling these core structures with various aldehydes, carboxylic acids, and alkynes to generate three separate libraries. High-throughput screening of the generated libraries with human N-acetyl-β-hexosaminidases produced only moderate inhibitory activities. However, the synthetic approach and screening strategy for these compounds will be applied to develop new potent inhibitors of human N-acetyl-β-hexosaminidases, particularly when combined with the structural information of these enzymes.
Syntheses of O-β-D-mannosyl-(1 → 4)-O-α-D-mannosyl-(1 → 3)-L-rhamnose and O-(2-acetamido-2-deoxy-β-D-mannosyl)-(1 → 4)-O-α-D-galactosyl-(1 → 4)-D-galactose via in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucose
Koto, Shinkiti,Shinoda, Yoshika,Hirooka, Motoko,Sekino, Akiko,Ishizumi, Sachiko,Koma, Mutsuko,Matuura, Chieko,Sakata, Naoko
, p. 1603 - 1615 (2007/10/03)
O-β-D-Mannopyranosyl-(1 → 4)-O-α-D-mannopyranosyl-(1 → 3)-L-rhamnopyranose, a trisaccharide including a repeating unit of the O-specific polysaccharide (OSP) of Bulkholderia vietnamiensis strain LMG 6988, and O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-(1 → 4)-O-α-D-galactopyranosyl-(1 → 4)-D-galactopyranose, a trisaccharide including a repeating unit of OSP of Acinetobactor baumannii serogroup O18, were synthesized by means of in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (2ATBG) and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and 1,8-diazabicyclo[5.4.0]undec-7-ene, and related systems. New syntheses of 2ATBG, allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, benzyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, and 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose are described.
A convenient multigram preparation of functionalized 2-azido-2-deoxy-D-mannose as a useful orthogonally protected building block for oligosaccharide synthesis
Draghetti, Veronica,Poletti, Laura,Prosperi, Davide,Lay, Luigi
, p. 813 - 819 (2007/10/03)
Multigram preparation of strategically protected 2-azido-2-deoxy mannose 5 from pentaacetyl glucose 1 is described. This manno-derivative was obtained in a straightforward manner and in high overall yield and represents a flexible building-block for complex oligosaccharide synthesis.
Preparation of diversely protected 2-azido-2-deoxyglycopyranoses from glycals
Czernecki,Ayadi
, p. 343 - 350 (2007/10/03)
A new and efficient preparation of diversely protected 2-azido-2-deoxyglycopyranosides from the corresponding glycals is described. The glycals are first transformed into protected phenyl 2-azido-2-deoxy-selenoglycopyranosides by azido-phenylselenylation.
New and Efficient Synthesis of Protected 2-Azido-2-deoxy-glycopyranoses from the Corresponding Glycal
Czernecki, Stanislas,Ayadi, Ebtissam,Randriamandimby, Dominique
, p. 35 - 36 (2007/10/02)
Diversely protected 2-azido-2-deoxy-D-glycopyranoses are prepared by azido phenylselenylation of the corresponding glycal followed by hydrolysis of the resulting selenoglycosides: from protected D-galactal, protected 2-azido-2-deoxy-D-galactopyranose is obtained, as the sole product in 72percent overall yield.
