Trp-Arg
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| Category | Others |
| Catalog number | BBF-05610 |
| CAS | 88831-09-8 |
| Molecular Weight | 360.41 |
| Molecular Formula | C17H24N6O3 |
| Purity | ≥95% by HPLC |
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Description
Tryptophanyl-arginine is a dipeptide composed of tryptophan and arginine. It is an incomplete breakdown product of protein digestion or protein catabolism.
Specification
| Related CAS | 276880-00-3 (dihydrochloride) |
| Synonyms | L-Arginine, L-tryptophyl-; tryptophanyl-arginine; L-tryptophyl-L-arginine; (S)-2-((S)-2-Amino-3-(1H-indol-3-yl)propanamido)-5-guanidinopentanoic acid |
| Sequence | H-Trp-Arg-OH |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)CC(C(=O)NC(CCCN=C(N)N)C(=O)O)N |
| InChI | InChI=1S/C17H24N6O3/c18-12(8-10-9-22-13-5-2-1-4-11(10)13)15(24)23-14(16(25)26)6-3-7-21-17(19)20/h1-2,4-5,9,12,14,22H,3,6-8,18H2,(H,23,24)(H,25,26)(H4,19,20,21)/t12-,14-/m0/s1 |
| InChI Key | LCPVBXOHXMBLFW-JSGCOSHPSA-N |
Properties
| Appearance | Solid |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Water |
Reference Reading
1. Comprehensive O-Glycosylation Analysis of the SARS-CoV-2 Spike Protein with Biomimetic Trp-Arg Materials
Xuefang Dong, Cheng Chen, Jingyu Yan, Xiaofei Zhang, Xiuling Li, Xinmiao Liang Anal Chem. 2021 Aug 3;93(30):10444-10452. doi: 10.1021/acs.analchem.0c04634. Epub 2021 Jul 20.
The COVID-19 pandemic caused by severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2) is a serious public health threat. Most vaccines against SARS-CoV-2 target the highly glycosylated spike protein (S). A good knowledge of the glycosylation profile of this protein is key to successful vaccine development. Unlike the 22 confirmed N-glycosylation sites on SARS-CoV-2 S, only a few O-glycosylation sites on this protein have been reported. This difference is mainly ascribed to the extremely low stoichiometry of O-glycosylation. Herein, we designed the biomimetic materials, Trp-Arg (WR) monomer-grafted silica microspheres (designated as WR-SiO2), and these biomimetic materials can enrich N- and O-linked glycopeptides with high selectivity. And WR-SiO2 can resist the nonglycopeptides' interference with the 100 molar fold of BSA during O-linked glycopeptide enrichment. We utilized WR-SiO2 to comprehensively analyze the O-glycosylation profile of recombinant SARS-CoV-2 S. Twenty-seven O-glycosylation sites including 18 unambiguous sites are identified on SARS-CoV-2 S. Our study demonstrates that the biomimetic polymer can offer specific selectivity for O-linked glycopeptides and pave the way for O-glycosylation research in biological fields. The O-glycosylation profile of SARS-CoV-2 S might supplement the comprehensive glycosylation in addition to N-glycosylation of SARS-CoV-2 S.
2. Modified histidine containing amphipathic ultrashort antifungal peptide, His[2-p-(n-butyl)phenyl]-Trp-Arg-OMe exhibits potent anticryptococcal activity
Krishna K Sharma, Ravikant Ravi, Indresh Kumar Maurya, Akshay Kapadia, Shabana I Khan, Vinod Kumar, Kulbhushan Tikoo, Rahul Jain Eur J Med Chem. 2021 Nov 5;223:113635. doi: 10.1016/j.ejmech.2021.113635. Epub 2021 Jun 12.
In pursuit of ultrashort peptide-based antifungals, a new structural class, His(2-aryl)-Trp-Arg is reported. Structural changes were investigated on His-Trp-Arg scaffold to demonstrate the impact of charge and lipophilic character on the biological activity. The presence and size of the aryl moiety on imidazole of histidine modulated overall amphiphilic character, and biological activity. Peptides exhibited IC50 of 0.37-9.66 μg/mL against C. neoformans. Peptide 14f [His(2-p-(n-butyl)phenyl)-Trp-Arg-OMe] exhibited two-fold potency (IC50 = 0.37 μg/mL, MIC = 0.63 μg/mL) related to amphotericin B, without any cytotoxic effects up to 10 μg/mL. Peptide 14f act by nuclear fragmentation, membranes permeabilization, disruption and pore formations in the microbial cells as determined by the mechanistic studies employing Trp-quenching, CLSM, SEM, and HR-TEM. The amalgamation of short sequence, presence of appropriate aryl group on l-histidine, potent anticryptococcal activity, no cytotoxicity, and detailed mechanistic studies directed to the identification of 14f as a new antifungal structural lead.
3. Total Synthesis of the Four Stereoisomers of Cyclo(l-Trp-l-Arg) Raises Uncertainty of the Structures of the Natural Products and Invalidates Their Promising Antimicrobial Activities
Dan Chen, Daniel J Park, Melissa M Cadelis, Hana Douafer, Marie Lise Bourguet-Kondracki, Jean Michel Brunel, Brent R Copp Molecules. 2022 Sep 12;27(18):5913. doi: 10.3390/molecules27185913.
New therapeutic options to combat the growing incidence of antimicrobial resistance are urgently needed. A 2015 publication reported the isolation and biological evaluation of two diketopiperazine natural products, cyclo(l-Trp-l-Arg) (CDP 2) and cyclo(d-Trp-d-Arg) (CDP 3), from an Achromobacter sp. bacterium, finding that the latter metabolite in particular exhibited strong antibacterial activity towards a range of wound-related microorganisms and could synergize the action of ampicillin. Intrigued by these biological activities and noting inconsistencies in the structural characterization of the natural products, we synthesized the four diastereomers of cyclo(Trp-Arg) and evaluated them for antimicrobial and antibiotic enhancement properties. The detailed comparison of spectroscopic data raises uncertainty regarding the structure of CDP 2 and disproves the structure of CDP 3. In our hands, none of the four stereoisomers of cyclo(Trp-Arg) exhibited detectable intrinsic antimicrobial properties towards a range of Gram-positive and Gram-negative bacteria or fungi nor could they potentiate the action of antibiotics. These discrepancies in biological properties, compared with the activities reported in the literature, reveal that these specific cyclic dipeptides do not represent viable templates for the development of new treatments for microbial infections.
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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 ╳
