Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic by Momcilo Miljkovic

By Momcilo Miljkovic

Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic results explains the conformational, electrostatic, and stereoelectronic components that keep an eye on the chemical and biochemical habit of carbohydrates in dwelling cells. subject matters comprise the anomeric influence, the chemistry of the glycosidic bond, isomerization of loose carbohydrates in aqueous options, relative reactivity of hydroxyl teams in carbohydrate molecules, and the addition of nucleophiles to glycopyranosiduloses. concentration then shifts to the synthesis of glycosidic bonds and oligosaccharides, the synthesis of anhydro and amino sugars, branched chain sugars and the security of hydroxyl teams in monosaccharides. The final 3 chapters are dedicated to parts usually missed in carbohydrate chemistry textbooks: carbohydrate dependent antibiotics, synthesis of polychiral ordinary items from carbohydrates, and the chemistry of higher-carbon sugars.

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The two hydrogens that point away from the ring and are almost parallel to the plane containing the four carbon atoms are said to be in bowsprit (b) orientation; the two hydrogens that are pointed toward the ring are said to be in flagpole ( f ) orientation. From other eight Conformational Analysis of Cyclic (Lactol, Hemiacetal) Forms of Monosaccharides 37 hydrogens four are equatorial and the other four pseudo-axial. Although the boat conformation is free from Baeyer (ring) strain, there is eclipsing of eight hydrogen atoms that are part of the planar part of the six-membered ring causing elevated torsional strain; in addition to that there is also a severe van der Waals interaction between two hydrogen atoms in the flagpole orientation.

The formation of tridentate complex involves the initial inversion of more stable chair form 71, in which the three hydroxyl groups are equatorially oriented, to the alternative chair conformation 72, in which they are all axial (Fig. 22). This conformation is then capable to form the borate complex. Tridentate complexes are formed in the 1:1 ratio from their components (cyclitols and borate) and are strong acids, unlike borate complexes with vicinal diols that are weak acids (the acid strength of the latter complexes is comparable to boric acid).

Since the equilibrium constants of tridentate borate formation depend on nonbonded interactions of the free hydroxyl groups, the values of these interaction energies were calculated from equilibrium constants (Figs. 25). The interaction energies are calculated in the following way. The energies of each nonbonded interaction in individual cyclitols, and in the tridentate borate complexes, are listed and separately added up. 0 (R=OH) H HO HO 74, R = H, scyllo-quercitol 75, R = OH, myo-inositol OH 76, R = H, scyllo-quercitol 77, R = OH, myo-inositol OH R OH OH B O R O + Borate HO OH O K = 310 (R=H) K = 700 (R=OH) OH H HO HO 78, R = H, epi-iquercitol 79, R = OH, epi-inositol H 80, R = H, epi-iquercitol 81, R = OH, epi-inositol Fig.

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