β-Casomorphin (1-7), bovine
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β-Casomorphin (1-7), bovine

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β-Casomorphin (1-7), bovine is an opioid peptide with an IC50 of 14 μM in an Opioid receptors binding assay.

Category
Peptide APIs
Catalog number
BAT-010122
CAS number
72122-62-4
Molecular Formula
C41H55N7O9
Molecular Weight
789.92
β-Casomorphin (1-7), bovine
IUPAC Name
(2S,3S)-2-[[(2S)-1-[2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-3-methylpentanoic acid
Synonyms
β-Casomorphin, bovine; β-Casomorphin-7 (bovine); Bovine β-casomorphin-7
Purity
≥97% by HPLC
Density
1.32 g/cm3
Boiling Point
1170.5°C at 760 mmHg
Sequence
YPFPGPI
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C41H55N7O9/c1-3-25(2)35(41(56)57)45-38(53)32-13-7-19-46(32)34(50)24-43-36(51)31-12-8-21-48(31)40(55)30(23-26-10-5-4-6-11-26)44-37(52)33-14-9-20-47(33)39(54)29(42)22-27-15-17-28(49)18-16-27/h4-6,10-11,15-18,25,29-33,35,49H,3,7-9,12-14,19-24,42H2,1-2H3,(H,43,51)(H,44,52)(H,45,53)(H,56,57)/t25-,29-,30-,31-,32-,33-,35-/m0/s1
InChI Key
RKYJTDSQXOMDAD-JKXTZXEVSA-N
Canonical SMILES
CCC(C)C(C(=O)O)NC(=O)C1CCCN1C(=O)CNC(=O)C2CCCN2C(=O)C(CC3=CC=CC=C3)NC(=O)C4CCCN4C(=O)C(CC5=CC=C(C=C5)O)N
1. Nanoelectrospray with ion-trap mass spectrometry for the determination of beta-casomorphins in derived milk products
Yolanda Picó,Ana Juan-García,Cristina Juan,Guillermina Font Talanta . 2009 Nov 15;80(1):294-306. doi: 10.1016/j.talanta.2009.06.062.
Beta-casomorphins (b-CMs) are bioactive peptides derived from casein with opioid agonist effects similar to morphine. The use of electrospray (ESI) with quadrupole ion-trap mass spectrometry (QIT-MS) for these compounds in two matrices, cheese and milk, was examined. It was compared to a liquid chromatography (LC) coupled to mass spectrometry (LC-MS), and a "soft" ionisation technique, NanoMate, with selected ion monitoring (SIM), which are unreliable for the determination of trace casomorphins in derived milk products. b-CM mass fragmentation pathways were done for the four most common b-CMs: beta-casomorphin (1-5) bovine (b-CM-5), beta-casomorphin (1-7) bovine (b-CM-7), [D-Ala2, D-Pro4,Tyr5]-beta-casomorphin (1-5) amide (b-CM-10) and beta-casomorphin (1-5) amide [D-Ala2,Hyp4,Tyr5] (b-CM-11). The major product ions obtained in QIT-MS were used to construct fragmentation pathways for b-CMs. The different collision energies using automated nanoelectrospray ion source NanoMate and conventional LC in QIT-MS were studied. Calibration data for b-CMs, using spiked milk or cheese samples (10 g or 10 mL), were: NanoMate/MS (25-1000 microg/L), r(2)=0.998; NanoMate/MS(2) (5-1000 microg/L), r(2)=0.9992; NanoMate/MS(3) (2.5-1000 microg/L), r(2)=0.9998. Reproducibility data (% RSD, N=5) for NanoMate/MS(n) mode ranged between 2.0 at 500 microg/L and 7.0 at 10 microg/L.
2. Effect of beta-casomorphin on neonatal sleep in rats
L A Hilakivi,J Aalto,T Taira,I Hilakivi Peptides . 1990 Jan-Feb;11(1):1-4. doi: 10.1016/0196-9781(90)90101-a.
The effects of bovine beta-casomorphin(1-7) (Tyr-Pro-Phe-Pro-Gly-Pro-Ile) on neonatal sleep in rats were studied. The pups received intraperitoneal injections of beta-casomorphin(1-7) (1 mg, 5 mg, 10 mg, 50 mg, or 100 mg/kg) or a corresponding volume of sodium chloride. In any of the doses used, beta-casomorphin(1-7) had no effect on waking. Only 100 mg/kg caused significant changes in sleep: the percentage of quiet state of the total recording time (TRT) increased and the percentage of active sleep decreased. Beta-casomorphin(1-7) did not cause significant respiratory depression. Naloxone pretreatment (1 mg/kg IP) reversed the effects of beta-casomorphin(1-7) on sleep, a finding which suggests that opiate mu-receptors are involved in mediating the sleep effects of beta-casomorphin.
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