Glycylglycine is the
dipeptide
A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiological ...
of
glycine
Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (G ...
, making it the simplest
peptide
Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides that have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty am ...
.
The compound was first synthesized by
Emil Fischer
Hermann Emil Louis Fischer (; 9 October 1852 – 15 July 1919) was a German chemist and List of Nobel laureates in Chemistry, 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He also developed the Fisch ...
and
Ernest Fourneau in 1901 by boiling
2,5-diketopiperazine
2,5-Diketopiperazine is an organic compound with the formula (NHCH2C(O))2. The compound features a six-membered ring containing two amide functional group, groups at opposite positions in the ring. It was first compound containing a peptide bo ...
(glycine anhydride) with hydrochloric acid.
Shaking with alkali
and other synthesis methods have been reported.
Because of its low toxicity, it is useful as a buffer for biological systems with effective ranges between
pH 2.5–3.8 and 7.5–8.9; however, it is only moderately stable for storage once dissolved. It is used in the synthesis of more complex peptides.
Glycylglycine has also been reported to be helpful in solubilizing recombinant proteins in ''E. coli''. Using different concentrations of the glycylglycine improvement in protein solubility after cell lysis has been observed.
References
{{wiktionary
Dipeptides
Dimers (chemistry)