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Glycosidic bonds of the form discussed above are known as O-glycosidic bonds, in reference to the glycosidic oxygen that links the glycoside to the aglycone or reducing end sugar. In analogy, one also considers S-glycosidic bonds (which form thioglycosides ), where the oxygen of the glycosidic bond is replaced with a sulfur atom.
Glycosynthase are derived from glycosidase enzymes, which catalyze the hydrolysis of glycosidic bonds. [2] They were traditionally formed from retaining glycosidase by mutating the active site nucleophilic amino acid (usually an aspartate or glutamate ) to a small non-nucleophilic amino acid (usually alanine or glycine ).
Chemical structure of DNA; hydrogen bonds shown as dotted lines. Each end of the double helix has an exposed 5' phosphate on one strand and an exposed 3′ hydroxyl group (—OH) on the other. DNA is a long polymer made from repeating units called nucleotides.
DNA structure and bases A-B-Z-DNA Side View. Tertiary structure refers to the locations of the atoms in three-dimensional space, taking into consideration geometrical and steric constraints. It is a higher order than the secondary structure, in which large-scale folding in a linear polymer occurs and the entire chain is folded into a specific 3 ...
(a) Three hydrogen bonding edges of the four nucleotides (Guanine), showing nomenclature of each edge and (b) Cis and Trans orientations of the sugar moieties of the two nucleotide residues glycosidic bonds of a base pair with respect to hydrogen bonding direction. The arrows in (b) indicate glycosidic bonds as vectors.
DNA glycosylases catalyze the first step of this process. They remove the damaged nitrogenous base while leaving the sugar-phosphate backbone intact, creating an apurinic/apyrimidinic site, commonly referred to as an AP site. This is accomplished by flipping the damaged base out of the double helix followed by cleavage of the N-glycosidic bond. [1]
Chemical structures for Watson–Crick and Hoogsteen A•T and G•C+ base pairs. The Hoogsteen geometry can be achieved by purine rotation around the glycosidic bond (χ) and base-flipping (θ), affecting simultaneously C8 and C1 ′ (yellow). [1] A Hoogsteen base pair is a variation of base-pairing in nucleic acids such as the A•T pair.
Structure of ONPG, an example of a β-galactoside. Depending on whether the glycosidic bond lies "above" or "below" the plane of the galactose molecule, galactosides are classified as α-galactosides or β-galactosides. A β-galactoside is a type of galactoside in which the glycosidic bond lies above the plane of the galactose residue.