L-Valyl-L-glutamic acid (BAT-006522)
* For research use only

Category
Others
Catalog number
BAT-006522
CAS number
3062-07-5
Molecular Formula
C10H18N2O5
Molecular Weight
246.26
L-Valyl-L-glutamic acid
Synonyms
Val-Glu-OH; Val Glu OH
Appearance
White solid
Purity
≥ 99% (TLC)
Storage
Store at 2-8°C
InChI
InChI=1S/C10H18N2O5/c1-5(2)8(11)9(15)12-6(10(16)17)3-4-7(13)14/h5-6,8H,3-4,11H2,1-2H3,(H,12,15)(H,13,14)(H,16,17)/t6-,8-/m0/s1
InChI Key
UPJONISHZRADBH-XPUUQOCRSA-N
Canonical SMILES
CC(C)C(C(=O)NC(CCC(=O)O)C(=O)O)N
1.Fractionation and characterization of antioxidant peptides derived from barley glutelin by enzymatic hydrolysis.
Xia Y1, Bamdad F, Gänzle M, Chen L. Food Chem. 2012 Oct 1;134(3):1509-18. doi: 10.1016/j.foodchem.2012.03.063. Epub 2012 Mar 23.
The antioxidant properties of the barley glutelin hydrolysates were evaluated based on their radical scavenging capacity (DPPH/O₂(·-)/OH(·)), Fe(2+)-chelating effect and reducing power. Alcalase hydrolysates (AH) demonstrated significantly higher antioxidant capacity than those treated by flavourzyme in most of the assays. The AH was separated using ultra-filtration and reversed-phase chromatography, and assessment of the fractions indicated that the large-sized peptides (Mw>10 kDa) possessed stronger DPPH scavenging activity and reducing power, whereas small-sized peptides (Mw<1 kDa) were more effective in Fe(2+)-chelating and OH(·) scavenging effect. The hydrophobic fraction contributed more to Fe(2+)-chelating and OH(·) scavenging activity. Four peptides contributing to antioxidant activities were identified using LC-MS/MS: Gln-Lys-Pro-Phe-Pro-Gln-Gln-Pro-Pro-Phe, Pro-Gln-Ile-Pro-Glu-Gln-Phe, Leu-Arg-Thr-Leu-Pro-Met and Ser-Val-Asn-Val-Pro-Leu.
2.Urantide conformation and interaction with the urotensin-II receptor.
Brancaccio D1, Limatola A, Campiglia P, Gomez-Monterrey I, Novellino E, Grieco P, Carotenuto A. Arch Pharm (Weinheim). 2014 Mar;347(3):185-92. doi: 10.1002/ardp.201300269. Epub 2013 Dec 4.
Urotensin II (U-II) is a disulfide bridged peptide hormone identified as the ligand of a G protein-coupled receptor. Human U-II (H-Glu-Thr-Pro-Asp-c[Cys-Phe-Trp-Lys-Tyr-Cys]-Val-OH) has been described as the most potent vasoconstrictor compound identified to date. We have previously identified the compound termed urantide (H-Asp-c[Pen-Phe-DTrp-Orn-Tyr-Cys]-Val-OH), which is the most potent UT receptor (UTR) antagonist described to date. Urantide may have potential clinical value in the treatment of atherosclerosis. In the present study, we studied the conformational preferences of urantide in DPC micelles and developed a urantide/UTR interaction model. This model can help the design of novel peptides and small molecules as UTR antagonists.
3.Identification of lipopeptide isoforms by MALDI-TOF-MS/MS based on the simultaneous purification of iturin, fengycin, and surfactin by RP-HPLC.
Yang H1, Li X, Li X, Yu H, Shen Z. Anal Bioanal Chem. 2015 Mar;407(9):2529-42. doi: 10.1007/s00216-015-8486-8. Epub 2015 Feb 10.
A three-stage linear gradient strategy using reverse-phase high-performance liquid chromatography (HPLC) was optimized for rapid, high-quality, and simultaneous purification of the lipopeptide isoforms of iturin, fengycin, and surfactin, which may differ in composition by only a single amino acid and/or the fatty acid residue. Matrix-assisted laser desorption ionization time-of-flight tandem mass spectrometry (MALDI-TOF-MS/MS) was applied to detect the lipopeptides harvested from each reversed-phase HPLC peak. Amino acid analysis based on phenyl isothiocyanate derivatization was further used for confirmation of the amino acid species and molar ratio in a certain HPLC fraction. By this MALDI-TOF-MS/MS coupled with amino acid analysis, it was revealed that iturin at m/z 1,043 consists of a circular Asn-Tyr-Asn-Gln-Pro-Asn-Ser peptide and C14 β-OH fatty acid. Surfactin homologs from Bacillus subtilis THY-7 at m/z 1,030, 1,044, 1,058, and 1,072 possess a circular Glu-Leu-Leu-Val-Asp-Leu-Leu peptide and the β-OH fatty acid with a different length (C13-C16).
4.New insight into the binding mode of peptides at urotensin-II receptor by Trp-constrained analogues of P5U and urantide.
Carotenuto A1, Auriemma L, Merlino F, Limatola A, Campiglia P, Gomez-Monterrey I, di Villa Bianca Rd, Brancaccio D, Santicioli P, Meini S, Maggi CA, Novellino E, Grieco P. J Pept Sci. 2013 May;19(5):293-300. doi: 10.1002/psc.2498. Epub 2013 Mar 25.
Urotensin II (U-II) is a disulfide bridged peptide hormone identified as the ligand of a G-protein-coupled receptor. Human U-II (H-Glu-Thr-Pro-Asp-c[Cys-Phe-Trp-Lys-Tyr-Cys]-Val-OH) has been described as the most potent vasoconstrictor compound identified to date. We have recently identified both a superagonist of human U-II termed P5U (H-Asp-c[Pen-Phe-Trp-Lys-Tyr-Cys]-Val-OH) and the compound termed urantide (H-Asp-c[Pen-Phe-D-Trp-Orn-Tyr-Cys]-Val-OH), which is the most potent UT receptor peptide antagonist described to date. In the present study, we have synthesized four analogues of P5U and urantide in which the Trp(7) residue was replaced by the highly constrained L-Tpi and D-Tpi residues. The replacement of the Trp(7) by Tpi led to active analogues. Solution NMR analysis allowed improving the knowledge on conformation-activity relationships previously reported on UT receptor ligands.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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