223590-83-8

Upstream product

• 29388-46-3 methyl 2,3-di-O-benzyl-α-D-galactopyranoside 
• 818-08-6 di(n-butyl)tin oxide 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 162680-20-8 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 
• 90633-88-8 methyl-2,3-bis-O-benzyl-4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 223590-86-1 methyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2,3-di-O-benzyl-6-O-benzoyl-α-D-(4-2H)-glucopyranoside 
• 223590-85-0 methyl 2,3-di-O-benzyl-6-O-benzoyl-α-D-(4-2H)-glucopyranoside 

Relevant academic research and scientific papers

Approaches to Pyranuronic β-Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers

Pyranuronic β-sugar amino acids (β-SAAs) are biocompatible and tuneable building blocks of foldamers and chimera-peptides. The scalable and economical total synthesis of two building blocks is described here. These C-4 epimers, Fmoc-GlcAPU(Me)-OH (7) and

Binding equilibrium isotope effects for glucose at the catalytic domain of human brain hexokinase

We have utilized tritium isotope effects to probe the in vitro binding equilibrium between glucose and human brain hexokinase (E.C.2.7.1.1). Replacing a backbone hydrogen atom in glucose with tritium can significantly increase or decrease the equilibrium association constant. Specifically, the equilibrium tritium isotope effects are 1.027 ± 0.002, 0.927 ± 0.0003, 1.027 ± 0.004, 1.051 ± 0.001, 0.988 ± 0.001, and 1.065 ± 0.003 for [1-t]-, [2-t]-, [3-t]-, [4-t]-, [5-t]-, and [6,6-t2]glucose, respectively. We have shown that the existence of prebinding equilibrium isotope effects can contribute to binding isotope effect studies but that this effect is insignificant for glucose binding to hexokinase. The binding isotope effects are interpreted in the context of structural studies of hexokinase - glucose complexes. Ab initio calculations on 2-propanol with or without a hydrogen bonding partner, in steric collision with formaldehyde or methane, and on ethanol, cyclohexanol and 1-hydroxymethyl-tetrahydropyran are presented to clarify the magnitude of isotope effects possible in such interactions and the accompanying changes in free energy. Position-specific binding isotope effects provide direct evidence of the partial deprotonation and activation of O6 by Asp657, of other hydrogen bonding interactions with ionic residues, and of the steric compression of CH2 by the backbone carbonyl of Ser603.

Oxidation of stannylene derivatives of carbohydrates using 1,3-dibromo-5,5-dimethylhydantoin

1,3-Dibromo-5,5-dimethylhydantoin (DBDMH) has been used to oxidize stannylene derivatives of monosaccharides to give hydroxy-ketones thereof. Oxidations could be performed rapidly and in good-to-excellent yields. The oxidizing reagent DBDMH thus provides