Dipeptide
Encyclopedia
A dipeptide is a molecule consisting of two amino acids joined by a single peptide bond
.
Dipeptides are produced from polypeptides by the action of the hydrolase
enzyme
dipeptidyl peptidase
. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids, because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin
.
The Bergmann azlactone peptide synthesis is a classic organic synthesis
for the preparation of dipeptides.
Peptide bond
This article is about the peptide link found within biological molecules, such as proteins. A similar article for synthetic molecules is being created...
.
Dipeptides are produced from polypeptides by the action of the hydrolase
Hydrolase
In biochemistry, a hydrolase is an enzyme that catalyzes the hydrolysis of a chemical bond. For example, an enzyme that catalyzed the following reaction is a hydrolase:-Nomenclature:...
enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
dipeptidyl peptidase
Dipeptidyl peptidase
Dipeptidyl peptidase is a type of enzyme classified under EC 3.4.14.Types include:* Cathepsin C, dipeptidyl peptidase-1* DPP3, dipeptidyl peptidase-3* Dipeptidyl peptidase-4* DPP6, dipeptidyl peptidase-6* DPP7, dipeptidyl peptidase-7...
. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids, because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin
Gastrin
In humans, gastrin is a peptide hormone that stimulates secretion of gastric acid by the parietal cells of the stomach and aids in gastric motility. It is released by G cells in the antrum of the stomach, duodenum, and the pancreas...
.
The Bergmann azlactone peptide synthesis is a classic organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
for the preparation of dipeptides.
Examples of dipeptides
- CarnosineCarnosineCarnosine is a dipeptide of the amino acids beta-alanine and histidine. It is highly concentrated in muscle and brain tissues....
(beta-alanyl-L-histidine) is highly concentrated in muscleMuscleMuscle is a contractile tissue of animals and is derived from the mesodermal layer of embryonic germ cells. Muscle cells contain contractile filaments that move past each other and change the size of the cell. They are classified as skeletal, cardiac, or smooth muscles. Their function is to...
and brain tissuesBrainThe brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...
. - AnserineAnserineAnserine is a dipeptide found in the skeletal muscle and brain of mammals, and birds.It is an antioxidant and helps reduce fatigue....
(beta-alanyl-N-methyl histidine) is found in the skeletal muscleSkeletal muscleSkeletal muscle is a form of striated muscle tissue existing under control of the somatic nervous system- i.e. it is voluntarily controlled. It is one of three major muscle types, the others being cardiac and smooth muscle...
and brain of mammalMammalMammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...
s. - Homoanserine (N-(4-aminobutyryl)-L-histidine) is another dipeptide identified in the brain and muscles of mammals.
- KyotorphinKyotorphinKyotorphin is a neuroactive dipeptide which plays a role in pain regulation in the brain. It was first isolated from bovine brain, by Japanese scientists in 1979. Kyotorphin was named for the site of its discovery, Kyoto, Japan and because of its morphine- like analgesic activity...
(L-tyrosyl-L-arginine) is a neuroactive dipeptide which plays a role in pain regulation in the brain. - Balenine (or ophidine) (beta-alanyl-N tau-methyl histidine) has been identified in the muscles of several species of mammal (including man), and the chickenChickenThe chicken is a domesticated fowl, a subspecies of the Red Junglefowl. As one of the most common and widespread domestic animals, and with a population of more than 24 billion in 2003, there are more chickens in the world than any other species of bird...
. - AspartameAspartameAspartame is an artificial, non-saccharide sweetener used as a sugar substitute in some foods and beverages. In the European Union, it is codified as E951. Aspartame is a methyl ester of the aspartic acid/phenylalanine dipeptide. It was first sold under the brand name NutraSweet; since 2009 it...
(N-L-α-aspartyl-L-phenylalanine 1-methyl ester) is an artificial sweetenerSugar substituteA sugar substitute is a food additive that duplicates the effect of sugar in taste, usually with less food energy. Some sugar substitutes are natural and some are synthetic. Those that are not natural are, in general, called artificial sweeteners....
. - Glorin (N-propionyl-γ-L-glutamyl-L-ornithine-δ-lac ethyl ester) is a chemotactic dipeptideChemotactic peptideChemotactic peptide is a formylated tripeptide produced by some types of bacteria. The amino acid sequence is N-formylmethionine, leucine, phenylalanine. It is a potent inducer of leucocyte chemotaxis and is also a macrophage activator....
for the slime-mould Polysphondylium violaceum. - Barettin (cyclo-[(6-bromo-8-en-tryptophan)-arginine]) is a cyclic dipeptideCyclic peptideCyclic peptides are polypeptide chains whose amino and carboxyl termini are themselves linked together with a peptide bond that forms a circular chain. A number of cyclic peptides have been discovered in nature and they can range anywhere from just a few amino acids in length, to hundreds...
from the marine sponge Geodia barretti. - PseudoprolinePseudoprolinePseudoproline derivatives are artificially created dipeptides to minimize aggregation during FMOC solid-phase synthesis of peptides.-Introduction:...
- GlycylglycineGlycylglycineGlycylglycine is the dipeptide of glycine, making it the simplest peptide.The compound was first synthesized by Emil Fischer and Ernest Fourneau in 1901 by boiling 2,5-diketopiperazine with hydrochloric acid....
External links
- An introduction to dipeptides at PeptideGuide.