beta-Casomorphin 5

• CAT Number: I014175
• CAS Number: 72122-63-5
• Molecular Formula: C30H37N5O7
• Molecular Weight: 579.65
• Purity: ≥95%
• Synonyms: beta-Casomorphin 5; 4-Pro-casomorphin; Deprolorphin; L-Pro(4)-casomorphin; Tyr-pro-phe-pro-gly;;L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolylglycine
• Target: opioid receptor agonist
• Solubility: Soluble in DMSO
• InChI: InChI=1S/C30H37N5O7/c31-22(16-20-10-12-21(36)13-11-20)29(41)34-14-5-9-25(34)28(40)33-23(17-19-6-2-1-3-7-19)30(42)35-15-4-8-24(35)27(39)32-18-26(37)38/h1-3,6-7,10-13,22-25,36H,4-5,8-9,14-18,31H2,(H,32,39)(H,33,40)(H,37,38)/t22-,23-,24-,25-/m0/s1
• InChIKey: PKKIDZFGRQACGB-QORCZRPOSA-N
• SMILES: O=C(O)CNC([C@H]1N(C([C@H](CC2=CC=CC=C2)NC([C@H]3N(C([C@H](CC4=CC=C(O)C=C4)N)=O)CCC3)=O)=O)CCC1)=O

Beta-Casomorphin 5 (CAT: I014175) is a naturally occurring opioid peptide derived from the breakdown of beta-casein, a protein found in milk. It has been identified as a fragment consisting of five amino acids. Beta-Casomorphin 5 has opioid-like properties and can interact with opioid receptors in the body, particularly the mu-opioid receptors. It is known to have analgesic (pain-relieving) effects and can also affect gastrointestinal function. Beta-Casomorphin 5 has been studied for its potential role in various physiological processes, including digestion, immune response, and neurological function.

Reference

1: Nguyen DD, Solah VA, Johnson SK, Charrois JW, Busetti F. Isotope dilution liquid chromatography-tandem mass spectrometry for simultaneous identification and quantification of beta-casomorphin 5 and beta-casomorphin 7 in yoghurt. Food Chem. 2014 Mar 1;146:345-52. doi: 10.1016/j.foodchem.2013.09.057. Epub 2013 Sep 18. PubMed PMID: 24176353.2: Sakaguchi M, Murayama K, Yabe K, Satoh M, Takeuchi M, Matsumura E. Beta-casomorphin-5 stimulates neurite outgrowth in a mouse neuroblastoma cell line (Neuro-2a). Neurosci Lett. 1998 Jul 24;251(2):97-100. PubMed PMID: 9718983.3: Dalziel JE, Spencer NJ, Dunstan KE, Lynch AT, Haggarty NW, Gopal PK, Roy NC. An in vitro rat model of colonic motility to determine the effect of β-casomorphin-5 on propagating contractions. Food Funct. 2014 Nov;5(11):2768-74. doi: 10.1039/c4fo00193a. PubMed PMID: 25093576.4: Liebmann C, Mentz P, Schnittler M, Schrader U, Neubert K, Barth A. Nonopioid effects of beta-casomorphin-5 in guinea pig heart: alterations to the beta-adrenoceptor-G-protein complex and inhibition of myocardial responses to isoproterenol. Peptides. 1991 Mar-Apr;12(2):265-70. PubMed PMID: 1648711.5: Ul Haq MR, Kapila R, Kapila S. Release of β-casomorphin-7/5 during simulated gastrointestinal digestion of milk β-casein variants from Indian crossbred cattle (Karan Fries). Food Chem. 2015 Feb 1;168:70-9. doi: 10.1016/j.foodchem.2014.07.024. Epub 2014 Jul 11. PubMed PMID: 25172685.6: Sakaguchi M, Koseki M, Wakamatsu M, Matsumura E. Effects of systemic administration of beta-casomorphin-5 on learning and memory in mice. Eur J Pharmacol. 2006 Jan 13;530(1-2):81-7. Epub 2005 Dec 15. PubMed PMID: 16360145.7: Sakaguchi M, Koseki M, Wakamatsu M, Matsumura E. Effects of beta-casomorphin-5 on passive avoidance response in mice. Biosci Biotechnol Biochem. 2003 Nov;67(11):2501-4. PubMed PMID: 14646221.8: Schmidt R, Neubert K, Barth A, Liebmann C, Schnittler M, Chung NN, Schiller PW. Structure-activity relationships of cyclic beta-casomorphin-5 analogues. Peptides. 1991 Nov-Dec;12(6):1175-80. PubMed PMID: 1667685.9: Ermisch A, Rühle HJ, Neubert K, Hartrodt B, Landgraf R. On the blood-brain barrier to peptides: [3H]beta-casomorphin-5 uptake by eighteen brain regions in vivo. J Neurochem. 1983 Nov;41(5):1229-33. PubMed PMID: 6619862.10: Hartrodt B, Neubert K, Fischer G, Schulz H, Barth A. [Synthesis and enzymatic degradation of beta-casomorphin-5 (author’s transl)]. Pharmazie. 1982 Mar;37(3):165-9. German. PubMed PMID: 7100234.11: Svedberg J, de Haas J, Leimenstoll G, Paul F, Teschemacher H. Demonstration of beta-casomorphin immunoreactive materials in in vitro digests of bovine milk and in small intestine contents after bovine milk ingestion in adult humans. Peptides. 1985 Sep-Oct;6(5):825-30. PubMed PMID: 4080604.12: Delaet NG, Verheyden PM, Tourwe D, Van Binst G, Davis P, Burks TF. Morphiceptin and beta-casomorphin-5 analogues containing a reduced peptide bond: selective mu-receptor agonists and a novel mu antagonist, H-Tyr-Pro psi (CH2-NH)Phe-Pro-Gly-OH. Biopolymers. 1992 Aug;32(8):957-69. PubMed PMID: 1330047.13: Blass EM, Blom J. beta-Casomorphin causes hypoalgesia in 10-day-old rats: evidence for central mediation. Pediatr Res. 1996 Feb;39(2):199-203. PubMed PMID: 8825787.14: Akhmedov NA. [Theoretical conformation analysis of beta-casomorphin-5 molecule]. Mol Biol (Mosk). 1986 Nov-Dec;20(6):1547-9. Russian. PubMed PMID: 3807911.15: Rüthrich HL, Grecksch G, Schmidt R. Phe1-substituted beta-casomorphin-5 analogues with analgesic activity. Peptides. 1994;15(3):457-60. PubMed PMID: 7937319.16: Delaet NG, Verheyden PM, Tourwé D, Van Binst G. Assignment of the 1H-NMR resonances of the four rotamers of beta-casomorphin-5 in DMSO. Biopolymers. 1991 Oct 15;31(12):1409-16. PubMed PMID: 1816877.17: Carpenter KA, Schiller PW, Schmidt R, Wilkes BC. Distinct conformational preferences of three cyclic beta-casomorphin-5 analogs determined using NMR spectroscopy and theoretical analysis. Int J Pept Protein Res. 1996 Jul;48(1):102-11. PubMed PMID: 8844269.18: Mentz P, Neubert K, Hoffmann S, Liebmann C, Barth A. Effects of beta-casomorphin in isolated heart preparations. Pharmazie. 1988 Apr;43(4):271-3. PubMed PMID: 3413218.19: Reymann KG, Chepkova AN, Schulzeck K, Ott T. Effects of beta-casomorphin on dentate hippocampal field potentials in freely moving rats. Biomed Biochim Acta. 1985;44(5):749-54. PubMed PMID: 2998350.20: Furkert J, Rathsack R, Schmidt HE. [Development of a radioimmunoassay for beta-casomorphin (1-5)]. Radiobiol Radiother (Berl). 1986;27(2):205-13. German. PubMed PMID: 3714988.