Tetrapeptide

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The tetrapeptide L-valinyl-glycyl-L-serinyl-L-alanine

A tetrapeptide is a peptide consisting of four amino acids joined by peptide bonds. Many tetrapeptides are pharmacologically active, often showing affinity and specificity for a variety of receptors in protein-protein signaling. Present in nature are both linear and cyclic tetrapeptides; tetrapeptides may be cyclized by a fourth peptide bond or other covalent bonds.

Examples of tetrapeptides are:

  • Tuftsin (L-threonyl-L-lysyl-L-prolyl-L-arginine) is a peptide related primarily to the immune system function.
  • Rigin (glycyl-L-glutaminyl-L-prolyl-L-arginine) is a tetrapeptide with functions similar to those of tuftsin.
  • Postin (Lys-Pro-Pro-Arg) is the N-terminal tetrapeptide of cystatin C and an antagonist of tuftsin.
  • Endomorphin-1 (H-Tyr-Pro-Trp-Phe-NH2) and endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2) are peptide amides with the highest known affinity and specificity for the μ opioid receptor.
  • Morphiceptin (H-Tyr-Pro-Phe-Pro-NH2) is a casomorphin peptide isolated from β-casein.
  • Gluten exorphines A4 (H-Gly-Tyr-Tyr-Pro-OH) and B4 (H-Tyr-Gly-Gly-Trp-OH) are peptides isolated from gluten.
  • Tyrosine-MIF-1 (H-Tyr-Pro-Leu-Gly-NH2) is an endogenous opioid modulator.
  • Tetragastrin (N-((phenylmethoxy)carbonyl)-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamide) is the C-terminal tetrapeptide of gastrin. It is the smallest peptide fragment of gastrin which has the same physiological and pharmacological activity as gastrin.
  • Kentsin (H-Thr-Pro-Arg-Lys-OH) is a contraceptive peptide first isolated from female hamsters.
  • Achatin-I (glycyl-phenylalanyl-alanyl-aspartic acid) is a neuroexcitatory tetrapeptide from giant African snail (Achatina fulica).
  • Tentoxin (cyclo(N-methyl-L-alanyl-L-leucyl-N-methyl-trans-dehydrophenyl-alanyl-glycyl)) is a natural cyclic tetrapeptide produced by phytopathogenic fungi from genus Alternaria.
  • GLYX-13 (H-Thr-Pro-Pro-Thr-NH2) is a partial agonist of the NMDA receptor.

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