337903-75-0

Upstream product

• 108-24-7 acetic anhydride 
• 337903-64-7 benzyl N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-benzoyl-2-deoxy-2-[(2,2,2-trichloroethyloxycarbonyl)amino]-β-D-glucopyranosyl)-L-serinate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 337903-44-3 2,2,2-trichloroethyloxycarbonyl-amino perbenzoylglucosamine 
• 219693-08-0 3,4,6-tri-O-benzoyl-2-deoxy-2-[(2,2,2-trichloroethoxycarbonyl)amino]-α-bromo-D-glucopyranose 

Relevant academic research and scientific papers

Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin

The synthesis of 18 N-α-FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-α-FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-α-FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-β(1-4)-Glc (lactose), Glc-β(1-4)-Glc (cellobiose), and Gal-α(1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-Phe-DCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.