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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.
A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon sugar (ribose or 2'-deoxyribose) whereas a nucleotide is composed of a nucleobase, a five-carbon sugar, and one or more phosphate groups. In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or the N1 of a ...
L-Ribose Fischer Projection. Ribose is a simple sugar and carbohydrate with molecular formula C 5 H 10 O 5 and the linear-form composition H−(C=O)−(CHOH) 4 −H. The naturally occurring form, d-ribose, is a component of the ribonucleotides from which RNA is built, and so this compound is necessary for coding, decoding, regulation and expression of genes.
Cytosine, thymine, and uracil are pyrimidines, hence the glycosidic bonds form between their 1 nitrogen and the 1' -OH of the deoxyribose. For both the purine and pyrimidine bases, the phosphate group forms a bond with the deoxyribose sugar through an ester bond between one of its negatively charged oxygen groups and the 5' -OH of the sugar. [2]
Cyclic ADP-ribose, frequently abbreviated as cADPR, is a cyclic adenine nucleotide (like cAMP) with two phosphate groups present on 5' OH of the adenosine (like ADP), further connected to another ribose at the 5' position, which, in turn, closes the cycle by glycosidic bonding to the nitrogen 1 (N 1) of the same adenine base (whose position N 9 has the glycosidic bond to the other ribose).
The source of ADP-ribose for most enzymes that perform this modification is the redox cofactor NAD +. In this transfer reaction, the N-glycosidic bond of NAD + that bridges the ADP-ribose molecule and the nicotinamide group is cleaved, followed by nucleophilic attack by the target amino acid side chain. (ADP-ribosyl)transferases can perform two ...
Guanosine (symbol G or Guo) is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N 9-glycosidic bond.Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP).
A riboside is any glycoside of ribose. [1] Ribosides in the form of ribonucleosides and ribonucleotides play an important role in biochemistry. References