Ile-His
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| Category | Others |
| Catalog number | BBF-05665 |
| CAS | 97284-12-3 |
| Molecular Weight | 268.31 |
| Molecular Formula | C12H20N4O3 |
| Purity | ≥95% by HPLC |
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Description
Isoleucyl-histidine is a dipeptide composed of isoleucine and histidine. It is an incomplete breakdown product of protein digestion or protein catabolism.
Specification
| Synonyms | Isoleucyl-Histidine; L-Ile-L-His |
| Sequence | H-Ile-His-OH |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid |
| Canonical SMILES | CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)O)N |
| InChI | InChI=1S/C12H20N4O3/c1-3-7(2)10(13)11(17)16-9(12(18)19)4-8-5-14-6-15-8/h5-7,9-10H,3-4,13H2,1-2H3,(H,14,15)(H,16,17)(H,18,19)/t7-,9-,10-/m0/s1 |
| InChI Key | QNBYCZTZNOVDMI-HGNGGELXSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 603.9±55.0 °C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Water |
Reference Reading
1. From Angiotensin IV to Small Peptidemimetics Inhibiting Insulin-Regulated Aminopeptidase
Mathias Hallberg, Mats Larhed Front Pharmacol. 2020 Oct 15;11:590855. doi: 10.3389/fphar.2020.590855. eCollection 2020.
It was reported three decades ago that intracerebroventricular injection of angiotensin IV (Ang IV, Val-Tyr-Ile-His-Pro-Phe) improved memory and learning in the rat. There are several explanations for these positive effects of the hexapeptide and related analogues on cognition available in the literature. In 2001, it was proposed that the insulin-regulated aminopeptidase (IRAP) is a main target for Ang IV and that Ang IV serves as an inhibitor of the enzyme. The focus of this review is the efforts to stepwise transform the hexapeptide into more drug-like Ang IV peptidemimetics serving as IRAP inhibitors. Moreover, the discovery of IRAP inhibitors by virtual and substance library screening and direct design applying knowledge of the structure of IRAP and of related enzymes is briefly presented.
2. Biocatalysis of D,L-Peptide Nanofibrillar Hydrogel
Tiziano Carlomagno, Maria C Cringoli, Slavko Kralj, Marina Kurbasic, Paolo Fornasiero, Paolo Pengo, Silvia Marchesan Molecules. 2020 Jun 30;25(13):2995. doi: 10.3390/molecules25132995.
Self-assembling peptides are attracting wide interest as biodegradable building blocks to achieve functional nanomaterials that do not persist in the environment. Amongst the many applications, biocatalysis is gaining momentum, although a clear structure-to-activity relationship is still lacking. This work applied emerging design rules to the heterochiral octapeptide sequence His-Leu-DLeu-Ile-His-Leu-DLeu-Ile for self-assembly into nanofibrils that, at higher concentration, give rise to a supramolecular hydrogel for the mimicry of esterase-like activity. The peptide was synthesized by solid-phase and purified by HPLC, while its identity was confirmed by 1H-NMR and electrospray ionization (ESI)-MS. The hydrogel formed by this peptide was studied with oscillatory rheometry, and the supramolecular behavior of the peptide was investigated with transmission electron microscopy (TEM) analysis, circular dichroism (CD) spectroscopy, thioflavin T amyloid fluorescence assay, and attenuated total reflectance (ATR) Fourier-transform infrared (FT-IR) spectroscopy. The biocatalytic activity was studied by monitoring the hydrolysis of p-nitrophenyl acetate (pNPA) at neutral pH, and the reaction kinetics followed an apparent Michaelis-Menten model, for which a Lineweaver-Burk plot was produced to determine its enzymatic parameters for a comparison with the literature. Finally, LC-MS analysis was conducted on a series of experiments to evaluate the extent of, if any, undesired peptide acetylation at the N-terminus. In conclusion, we provide new insights that allow gaining a clearer picture of self-assembling peptide design rules for biocatalysis.
3. Heterotrimeric Gq proteins act as a switch for GRK5/6 selectivity underlying β-arrestin transducer bias
Kouki Kawakami, Masataka Yanagawa, Suzune Hiratsuka, Misaki Yoshida, Yuki Ono, Michio Hiroshima, Masahiro Ueda, Junken Aoki, Yasushi Sako, Asuka Inoue Nat Commun. 2022 Jan 25;13(1):487. doi: 10.1038/s41467-022-28056-7.
Signaling-biased ligands acting on G-protein-coupled receptors (GPCRs) differentially activate heterotrimeric G proteins and β-arrestins. Although a wealth of structural knowledge about signaling bias at the GPCR level exists (preferential engagement of a specific transducer), little is known about the bias at the transducer level (different functions mediated by a single transducer), partly due to a poor understanding of GPCR kinase (GRK)-mediated GPCR phosphorylation. Here, we reveal a unique role of the Gq heterotrimer as a determinant for GRK-subtype selectivity that regulates subsequent β-arrestin conformation and function. Using the angiotensin II (Ang II) type-1 receptor (AT1R), we show that β-arrestin recruitment depends on both GRK2/3 and GRK5/6 upon binding of Ang II, but solely on GRK5/6 upon binding of the β-arrestin-biased ligand TRV027. With pharmacological inhibition or genetic loss of Gq, GRK-subtype selectivity and β-arrestin functionality by Ang II is shifted to those of TRV027. Single-molecule imaging identifies relocation of AT1R and GRK5, but not GRK2, to an immobile phase under the Gq-inactive, AT1R-stimulated conditions. These findings uncover a previously unappreciated Gq-regulated mechanism that encodes GRK-subtype selectivity and imparts distinct phosphorylation-barcodes directing downstream β-arrestin functions.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
