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A dipeptide is a sometimes ambiguous designation of two classes of organic compounds: Its molecules contain either two amino acids joined by a single peptide bond or one amino acid with two peptide bonds.

Two amino acids, one peptide bond[edit]

In this usage, X dipeptide (with X designating an amino acid) must be understood as di-X peptide. This nomenclature is continued by tripeptide (three amino acids, two peptide bonds), tetrapeptide, and so on; longer chains are called oligopeptide, polypeptide, protein.

Glycylglycine

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.^[1]^[2]

Examples[edit]

Carnosine (beta-alanyl-L-histidine) is highly concentrated in muscle and brain tissues.
Anserine (beta-alanyl-N-methyl histidine) is found in the skeletal muscle and brain of mammals.
Homoanserine (N-(4-aminobutyryl)-L-histidine) is another dipeptide identified in the brain and muscles of mammals.
Kyotorphin (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 chicken.
Aspartame (N-L-α-aspartyl-L-phenylalanine 1-methyl ester) is an artificial sweetener.
Glorin (N-propionyl-γ-L-glutamyl-L-ornithine-δ-lac ethyl ester) is a chemotactic dipeptide for the slime-mould Polysphondylium violaceum.
Barettin (cyclo-[(6-bromo-8-en-tryptophan)-arginine]) is a cyclic dipeptide from the marine sponge Geodia barretti.
Pseudoproline
Glycylglycine

One amino acid, two peptide bond[edit]

In this usage, X dipeptide is taken literally: One amino acid X is equipped with two minimal peptide bonds: The C terminus COOH becomes COCH₃, the N terminus NH₂ becomes NHCH₃. For instance, alanine dipeptide is CH₃CONHCH(CH₃)CONHCH₃.^[3]

References[edit]

^ M. Bergmann et al., Ann. 449, 277 (1926)
^ drugfuture.com Link
^ T. Head-Gordon et al, A theoretical study of alanine dipeptide and analogs. International Journal of Quantum Chemistry 36, 311 (1989).

External links[edit]

An introduction to dipeptides at PeptideGuide.

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English Journal

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Isolation of a novel calcium-binding peptide from wheat germ protein hydrolysates and the prediction for its mechanism of combination.

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Japanese Journal

魚類におけるイミダゾールジペプチドの機能性 (特集機能性ペプチド : 利用の現状と展望) -- (天然ペプチドの生理機能)

吉川尚子
冷凍 90(1049), 141-144, 2015-03
NAID 40020399614

Bioactive and Taste-related Compounds in Defatted Freeze-dried Chicken Soup Made from Two Different Chicken Breeds Obtained at Retail

, , , , ,
The Journal of Poultry Science 52(2), 156-165, 2015
… The betaine, carnitine, histidine dipeptide, creatine, nucleotide, free amino acid content, and fatty acid composition were analyzed in six DFDS samples from each breed. …
NAID 130005068571

Collagen-derived dipeptide prolyl-hydroxyproline promotes differentiation of MC3T3-E1 osteoblastic cells

君羅好史,小倉香名,谷内友梨,片岡綾,井上直紀,Sugihara Fumihito,中谷祥恵,清水純,和田政裕,真野博
Biochemical and Biophysical Research Communications 453(3), 498-501, 2014-10-24
Prolyl-hydroxyproline (Pro-Hyp) is one of the major constituents of collagen-derived dipeptides. The objective of this study was to investigate the effects of Pro-Hyp on the proliferation and differen …
NAID 120005528643