Phenylalanyl-lysine
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| Category | Others |
| Catalog number | BBF-05509 |
| CAS | 6456-72-0 |
| Molecular Weight | 293.36 |
| Molecular Formula | C15H23N3O3 |
| Purity | ≥95% |
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Description
Phenylalanyl-lysine is a dipeptide composed of phenylalanine and lysine. It is an incomplete breakdown product of protein digestion or protein catabolism.
Specification
| Synonyms | 3-Phenyl-L-Ala-L-Lys-OH; L-Phe-L-Lys-OH; N2-(3-Phenyl-L-alanyl)-L-lysine; Phe-Lys-OH; L-Lysine, L-phenylalanyl-; (S)-6-Amino-2-((S)-2-amino-3-phenyl-propionylamino)-hexanoic acid; H-FK-OH; L-phenylalanyl-L-lysine |
| Sequence | H-Phe-Lys-OH |
| IUPAC Name | (2S)-6-amino-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]hexanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)CC(C(=O)NC(CCCCN)C(=O)O)N |
| InChI | InChI=1S/C15H23N3O3/c16-9-5-4-8-13(15(20)21)18-14(19)12(17)10-11-6-2-1-3-7-11/h1-3,6-7,12-13H,4-5,8-10,16-17H2,(H,18,19)(H,20,21)/t12-,13-/m0/s1 |
| InChI Key | FADYJNXDPBKVCA-STQMWFEESA-N |
Properties
| Appearance | Solid |
| Boiling Point | 569.7±50.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Insights into the Activation Mechanism of the ALX/FPR2 Receptor
Vinicius Schmitz Nunes, Alexandre P Rogério, Odonírio Abrahão Jr J Phys Chem Lett. 2020 Nov 5;11(21):8952-8957. doi: 10.1021/acs.jpclett.0c02052. Epub 2020 Oct 8.
The formyl peptide receptor 2 (ALX/FPR2), a G-protein-coupled receptor (GPCR), plays an important role in host defense and inflammation. This receptor can be driven as pro- or anti-inflammatory depending on its agonist, such as N-formyl-Met-Leu-Phe-Lys (fMLFK) and resolvin D1 (RvD1) or its aspirin-triggered 17 (R)-epimer, AT-RvD1, respectively. However, the activation mechanism of ALX/FPR2 by pro- and anti-inflammatory agonists remains unclear. In this work, on the basis of molecular dynamics simulations, we evaluated a model of the ALX/FPR2 receptor activation process using two agonists, fMLFK and AT-RvD1, with opposite effects. The simulations by both fMLFK and AT-RvD1 induced the ALX/FPR2 activation through a set of receptor-core residues, in particular, R205, Q258, and W254. In addition, the activation was dependent on the disruption of electrostatic interactions in the cytoplasmic region of the receptor. We also found that in the AT-RvD1 simulations, the position of the H8 helix was similar to that of the same helix in other class-A GPCRs coupled to arrestin. Thus our results shed light on the mechanism of activation of the ALX/FPR2 receptor by pro-inflammatory and pro-resolution agonists.
2. Antimicrobial peptide KSL-W and analogues: Promising agents to control plant diseases
Cristina Camó, Anna Bonaterra, Esther Badosa, Aina Baró, Laura Montesinos, Emilio Montesinos, Marta Planas, Lidia Feliu Peptides. 2019 Feb;112:85-95. doi: 10.1016/j.peptides.2018.11.009. Epub 2018 Nov 30.
Recent strong restrictions on the use of pesticides has prompted the search for safer alternatives, being antimicrobial peptides promising candidates. Herein, with the aim of identifying new agents, 15 peptides reported as plant defense elicitors, promiscuous, multifunctional or antimicrobial were selected and tested against six plant pathogenic bacteria of economic importance. Within this set, KSL-W (KKVVFWVKFK-NH2) displayed high antibacterial activity against all the tested pathogens, low hemolysis and low phytotoxicity in tobacco leaves. This peptide was taken as a lead and 49 analogues were designed and synthesized, including N-terminal deletion sequences, peptides incorporating a d-amino acid and lipopeptides. The screening of these sequences revealed that a nine amino acid length was the minimum for activity. The presence of a d-amino acid significantly decreased the hemolysis and endowed KSL-W with the capacity to induce the expression of defense-related genes in tomato plants. The incorporation of an acyl chain led to sequences with high activity against Xanthomonas strains, low hemolysis and phytotoxicity. Therefore, this study demonstrates that KSL-W constitutes an excellent candidate as new agent to control plant diseases and can be considered as a lead to develop derivatives with multifunctional properties, including antimicrobial and plant defense elicitation.
3. Self-Assembly and Enzyme Responsiveness of Amphiphilic Linear-Dendritic Block Copolymers Based on Poly( N-vinylpyrrolidone) and Dendritic Phenylalanyl-lysine Dipeptides
Junwu Wei, Feng Lin, Dan You, Yangyang Qian, Yujia Wang, Yunmei Bi Polymers (Basel). 2019 Oct 8;11(10):1625. doi: 10.3390/polym11101625.
In this study, we present the synthesis, self-assembly, and enzyme responsive nature of a unique class of well-defined amphiphilic linear-dendritic block copolymers (PNVP-b-dendr(Phe-Lys)n, n = 1-3) based on linear poly(N-vinylpyrrolidone) (PNVP) and dendritic phenylalanyl-lysine (Phe-Lys) dipeptides. The copolymers were prepared via a combination ofreversible addition-fragmentation chain transfer (RAFT) /xanthates (MADIX) polymerization of N-vinylpyrrolidone and stepwise peptide chemistry. The results of fluorescence spectroscopy, 1H NMR analyses, transmission electron microscopy (TEM), and particle size analysis demonstrated that the copolymers self-assemble in aqueous solution into micellar nanocontainers that can disassemble and release encapsulated anticancer drug doxorubicin or hydrophobic dye Nile red by trigger of a serine protease trypsin under physiological conditions. The disassembly of the formed micelles and release rates of the drug or dye can be adjusted by changing the generation of dendrons in PNVP-b-dendr(Phe-Lys)n. Furthermore, the cytocompatibility of the copolymers have been confirmed using human lung epithelial cells (BEAS-2B) and human liver cancer cells (SMMC-7721). Due to the fact of their enzyme responsive properties and good biocompatibility, the copolymers may have potential applicability in smart controlled release systems capable of site-specific response.
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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 ╳
