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Attempts to synthesize 4-deoxy-4-fluoro-KRN-7000 ( 2 ), a potential immune adjuvant, by fluorination of 4-hydroxy of α- d -glucopyranoside using DAST, were not successful. Instead, the unusual 5-deoxy-5-fluoro β- l -altrofurnoside and the corresponding 4-deoxy-4-fluoro α- d -glucopyranoside with retained configuration were obtained. In the presence of polar solvents, the reaction afforded the epoxide product, suggesting the bicyclic oxiranium ion intermediate to be involved in this reaction. Compound 2 was eventually achieved by treating 4-methanesufonated glucopyranoside with fluoride ion and found to be a weak agonist for CD1d and NKT cell activation. [ABSTRACT FROM AUTHOR]

Abstract: Novel C-aryl-d-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50 =0.62μM). [Copyright &y& Elsevier]

• Analysis of Conc. of chondroitin sulfate (CS) of osteoarthritis (OA) cartilages. • Total CS and chondroitin-4-sulfate, were significantly lowered in OA cartilages. • The first microstructure analysis of CS in the OA cartilages. • Sulfotransferases, for CS sulfation, are down-regulated in OA cartilages. Chondroitin sulfates (CS) account for more than 80% of the glycosaminoglycans of articular cartilage, which impart its physiological functions. We quantified the absolute concentration of the CS components of the full thickness cartilages from the knees of patients with terminal-phase osteoarthritis. Osteochondrol biopsies were removed from the medial femoral condyle and lateral femoral condyle of sixty female patients received total knee arthroplasty, aged from 58 to 83 years old. We found the total CS concentrations and chondroitin-4-sulfate disaccharide were significantly lowered in osteoarthritic samples. Microstructure analysis indicated while chondroitin-0-sulfate was equally distributed across different zones of the osteoarthritic cartilages, chondroitin-4-sulfate is significantly less in the deep zones. Down-regulation of sulfotransferases, the enzymes responsible for CS sulfation, in the lesion site of cartilage were observed. Our study suggested chondroitin-4-sulfate down-regulation can be a diagnostic marker for degraded osteoarthritis cartilage, with potential implications in cartilage regeneration. [ABSTRACT FROM AUTHOR]