Asparagine

Asparagine is a protein-building amino acid with the side chain –CH₂CONH₂. Its codons in the standard genetic code are AAU and AAC.

Amino acid: An organic molecule with both an amino group and a carboxyl group; amino acids build proteins. Asparagine is one of the amino acids incorporated into proteins.
Hydrogen bond: An attractive interaction involving a hydrogen bonded to an electronegative atom and another electronegative atom. Asparagine’s side-chain carbonyl and amide can participate in hydrogen bonding.
Acrylamide: A small organic compound used industrially and formed in some foods during high-temperature cooking. Asparagine can react with reducing sugars to form acrylamide during heating.
Aspartic acid: An acidic amino acid with a side-chain carboxyl group that is usually negatively charged at physiological pH. It differs from asparagine by replacing the side-chain amide with a carboxyl group.
Amide: An organic functional group in which a carbonyl carbon is bonded to nitrogen. Asparagine’s side chain contains a carboxamide group.
N-linked glycosylation: The attachment of an oligosaccharide to the nitrogen of an asparagine side chain in a protein. This protein modification occurs at particular asparagine residues.
Maillard reaction: A set of reactions between amino compounds and reducing sugars that produce browned, flavor-rich products. Asparagine participates in food-browning chemistry that can also produce acrylamide.
Glutamine: A polar, uncharged amino acid with the side chain –CH₂CH₂CONH₂. Glutamine has the same terminal amide as asparagine but one additional side-chain methylene.
Polar uncharged amino acid: An amino acid whose side chain is polar but usually carries no net charge at physiological pH. Asparagine’s side chain can form hydrogen bonds without carrying a typical physiological charge.
N-glycosylation sequon: A protein sequence motif, Asn-X-Ser or Asn-X-Thr, that can be recognized for N-linked glycosylation. A suitable sequence context determines whether an asparagine can receive an N-linked glycan.

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ThreonineCompared with: Asparagine is polar like threonine but lacks a side-chain hydroxyl group.