Tripeptides

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A linear tripeptide (such as Val - Gly - Ala ) with a
green marked N-terminal α-amino acid residue (in the example: L -valine ) and a blue- marked C-terminal α-amino acid residue (in the example: L -alanine )
Glutathione tripeptide with a green -labeled N-terminal γ-L-glutamyl residue and blue labeled C-terminal glycyl residue
Cyclotriprolyl a cyclic tripeptide made up of three residues of the amino acid L- proline.

Tripeptides are peptides made up of three amino acid residues and belong to the group of oligopeptides . Like other oligopeptides, tripeptides often have a very specific physiological effect, e.g. B. in neurochemistry , in metabolism and as releasing hormones . Proteins are broken down into amino acids, dipeptides and tripeptides in the course of digestion by peptidases . Tripeptides are taken up in the small intestine and the kidneys via the peptide transporter 1 . Tripeptidyl-peptidases are peptidases that split off tripeptides.

Examples

Examples of naturally occurring tripeptides include the antioxidants glutathione , ophthalmic acid , the protease inhibitor leupeptin , the melanotropin release inhibiting hormone , the lactotripeptides , GHK-Cu and the herbicide Bialaphos . Some natural tripeptides have an amide at the C terminus , such as thyreoliberin and the melanocyte-inhibiting factor . The peptide alkaloids among the ergot alkaloids contain, among other things, a tripeptide. One non-ribosomally produced peptide is the ACV tripeptide . Synthetic tripeptides are the ACE inhibitors lisinopril , enalapril and ramipril as well as neuroprotective analogues of thyreoliberin.

literature

  • S. Santos, I. Torcato, MA Castanho: Biomedical applications of dipeptides and tripeptides. In: Biopolymers. Volume 98, Number 4, 2012, pp. 288-293, PMID 23193593 .

See also

Individual evidence

  1. ↑ M. Rothe, K.-D. Steffen, I. Rothe: Synthesis of cyclo-tri-L-prolyl, a cyclo-tri-peptide with a nine-membered ring, Angewandte Chemie 77, 1965, pp. 347-348.
  2. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 6: T-Z. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1988, ISBN 3-440-04516-1 , p. 4360.
  3. ↑ G. Wu: Dietary protein intake and human health. In: Food & function. Volume 7, Number 3, March 2016, pp. 1251-1265, doi : 10.1039 / c5fo01530h , PMID 26797090 .
  4. ↑ T. Terada, K. Inui: Recent advances in structural biology of peptide transporters. In: Current topics in membranes. Volume 70, 2012, pp. 257-274, doi : 10.1016 / B978-0-12-394316-3.00008-9 , PMID 23177989 .
  5. ^ AI Faden, SM Knoblach, VA Movsesyan, PM Lea, I. Cernak: Novel neuroprotective tripeptides and dipeptides. In: Annals of the New York Academy of Sciences. Volume 1053, August 2005, pp. 472-481, doi : 10.1196 / annals.1344.041 , PMID 16179555 .