ⓘ Dehydroamino acid. In biochemistry, a dehydroamino acid is an amino acids, usually with a C=C double bond in its side chain. Dehydroamino acids are not coded by ..

                                     

ⓘ Dehydroamino acid

In biochemistry, a dehydroamino acid is an amino acids, usually with a C=C double bond in its side chain. Dehydroamino acids are not coded by DNA, but arise via post-transcriptional modification.

                                     

1. Examples

A common dehydroamino acid is dehydroalanine, which otherwise exists only as a residue in proteins and peptides. The dehydroalanine residue is obtained dehydration of serine-containing protein/peptide. as well as removal of H 2 S from cysteine. Another example is dehydrobutyrine, derived from dehydration of threonine.

Generally, amino acid residues are unreactive toward nucleophiles, but the dehydroamino acids are exceptions to this pattern. For example, dehydroalanine adds cysteine and lysine to form covalent crosslinks.

An unusual dehydroamino acid is dehydroglycine DHG because it does not contain a carbon-carbon double bond. Instead it is the imine of glyoxalic acid. It arises by the radical-induced degradation of tyrosine.

                                     

2. N-Acyl derivatives

Dehydroamino acids do not feature amino-alkene groups, but the corresponding N-acylated derivatives are known. These derivatives, also known as N-acylamino acrylates, are prochiral substrates for asymmetric hydrogenation. The 2001 Nobel Prize in Chemistry was awarded to William S. Knowles for his synthesis of L -DOPA from the N-acylacrylate.

Free and no ads
no need to download or install

Pino - logical board game which is based on tactics and strategy. In general this is a remix of chess, checkers and corners. The game develops imagination, concentration, teaches how to solve tasks, plan their own actions and of course to think logically. It does not matter how much pieces you have, the main thing is how they are placement!

online intellectual game →