By Momcilo Miljkovic
Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic results explains the conformational, electrostatic, and stereoelectronic elements that keep an eye on the chemical and biochemical habit of carbohydrates in residing cells. issues contain the anomeric impression, the chemistry of the glycosidic bond, isomerization of unfastened carbohydrates in aqueous suggestions, 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 frequently missed in carbohydrate chemistry textbooks: carbohydrate established antibiotics, synthesis of polychiral typical items from carbohydrates, and the chemistry of higher-carbon sugars.
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Extra info for Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects
12): chair 32, boat 33, and twist-boat (or skew-boat) 34 conformations. The chair conformation is relatively stiff and has the following elements of symmetry: C3 axis of symmetry that coincides with the S6 rotation–reﬂection axis of symmetry, three C2 axis of symmetry, three planes of symmetry, and a center of symmetry. The boat conformation is ﬂexible and has one C2 axis of symmetry and two planes of symmetry, whereas the skew-boat (or twist-boat) conformation is ﬂexible and has no symmetry elements.
The proof that furanoses do exist in nonplanar conformations has been obtained from X-ray crystallographic studies as well as from NMR spectroscopy studies in solutions. Depending on the nature and location of its substituents, the furanose ring was shown to adopt both the Cs and the C2 conformation [29–33]. Bulky substituents are taking up the most staggered (“equatorial”) position, at the most staggered carbon atom. The oxygen atom most likely takes up the least staggered position in the furanose ring.
4). The anti/gauche conformer ratio in n-butane is, at room temperature, almost 2:1 as determined by NMR spectroscopy. Consequently, the polymethylene hydrocarbons tend to adopt planar zigzag conformation in which all carbon atoms lie in one plane (Fig. 6). ). ) are the only destabilizing interactions. Unlike the acyclic hydrocarbons, each carbon atom of an acyclic monosaccharide has in addition to a hydrogen atom one large substituent which is most often hydroxyl group, but it can also be an amino, thio, or other group or an atom.
Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects by Momcilo Miljkovic