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Glutamine (symbol Gln or Q) [3] is an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced by an amide. It is classified as a charge-neutral, polar amino acid.
Deamidation is a chemical reaction in which an amide functional group in the side chain of the amino acids asparagine or glutamine is removed or converted to another functional group. Typically, asparagine is converted to aspartic acid or isoaspartic acid. Glutamine is converted to glutamic acid or pyroglutamic acid (5-oxoproline).
This occurs halfway between the two carboxylate pK a values: pI = 1 / 2 (pK a1 + pK a(R)), where pK a(R) is the side chain pK a. [38] Similar considerations apply to other amino acids with ionizable side-chains, including not only glutamate (similar to aspartate), but also cysteine, histidine, lysine, tyrosine and arginine with positive ...
Amino acids such as lysine, glutamic acid, glutamine, aspartic acid, and asparagine can form isopeptide bonds because they all contain an amino or carboxyl group on their side chain. For example, the formation of an isopeptide bond between the sidechains of lysine and glutamine is as follows: Gln−(C=O)NH 2 + Lys-NH 3 + → Gln−(C=O)NH−Lys ...
Glutamine synthetase (GS) (EC 6.3.1.2) [3] ... Adenylylation is a post-translational modification involving the covalent attachment of AMP to a protein side chain.
Transglutaminases can also join a primary amine ( RNH 2 ) to the side chain carboxyamide group of a protein/peptide bound glutamine residue thus forming an isopeptide bond [1] Gln-(C=O)NH 2 + RNH 2 → Gln-(C=O)NHR + NH 3. These enzymes can also deamidate glutamine residues to glutamic acid residues in the presence of water [1]
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[4] [5] The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid ( R−C(=O)−OH ) with the hydroxyl group ( −OH ) replaced by an amine group ( −NR′R″ ); or ...
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