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The table sugar used in everyday vernacular is itself a disaccharide sucrose comprising one molecule of each of the two monosaccharides D-glucose and D-fructose. [ 2 ] Each carbon atom that supports a hydroxyl group is chiral , except those at the end of the chain.
l-Glucose is an organic compound with formula C 6 H 12 O 6 or O=CH[CH(OH)] 5 H, specifically one of the aldohexose monosaccharides. As the l-isomer of glucose, it is the enantiomer of the more common d-glucose. l-Glucose does not occur naturally in living organisms, but can be synthesized in the laboratory.
The earlier notation according to the rotation of the plane of linearly polarized light (d and l-nomenclature) was later abandoned in favor of the d - and l-notation, which refers to the absolute configuration of the asymmetric center farthest from the carbonyl group, and in concordance with the configuration of d - or l-glyceraldehyde. [14] [15]
An oligosaccharide has both a reducing and a non-reducing end. The reducing end of an oligosaccharide is the monosaccharide residue with hemiacetal functionality, thereby capable of reducing the Tollens’ reagent, while the non-reducing end is the monosaccharide residue in acetal form, thus incapable of reducing the Tollens’ reagent. [2]
These prefixes are attached to the systematic name of the molecular graph. So for example, D-glucose is D-gluco-hexose, D-ribose is D-ribo-pentose, and D-psicose is D-ribo-hexulose. Note that, in this nomenclature, mirror-image isomers differ only in the ' D '/' L ' prefix, even though all their hydroxyls are reversed.
The stereochemical configuration can only be determined from the chemical structure, whereas the optical rotation can only be determined empirically (by experiment). It was by a lucky guess that the molecular D-geometry was assigned to (+)-glyceraldehyde in the late 19th century, as confirmed by X-ray crystallography in 1951. [5]
For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.[note 1] However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin.
By the Fischer convention, glucuronic acid has two stereoisomers (enantiomers), D- and L-glucuronic acid, depending on its configuration at C-5. Most physiological sugars are of the D-configuration. Due to ring closure, cyclic sugars have another asymmetric carbon atom (C-1), resulting in two more stereoisomers, named anomers. Depending on the ...