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N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

Phosphopeptide ligand for src SH2 domain CAS# 190078-50-3

N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

2D Structure

Catalog No. BCC5855----Order now to get a substantial discount!

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3D structure

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N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

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Chemical Properties of N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

Cas No. 190078-50-3 SDF Download SDF
PubChem ID 444112 Appearance Powder
Formula C26H42N3O9P M.Wt 571.61
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Sequence YE

(Modifications: Tyr-1 = N-Ac-p-Tyr, Glu-2 = Glu-dipentylamide)

Chemical Name (4S)-4-[[(2S)-2-acetamido-3-(4-phosphonooxyphenyl)propanoyl]amino]-5-(dipentylamino)-5-oxopentanoic acid
SMILES CCCCCN(CCCCC)C(=O)C(CCC(=O)O)NC(=O)C(CC1=CC=C(C=C1)OP(=O)(O)O)NC(=O)C
Standard InChIKey LMADZBIAOYLZDD-GOTSBHOMSA-N
Standard InChI InChI=1S/C26H42N3O9P/c1-4-6-8-16-29(17-9-7-5-2)26(34)22(14-15-24(31)32)28-25(33)23(27-19(3)30)18-20-10-12-21(13-11-20)38-39(35,36)37/h10-13,22-23H,4-9,14-18H2,1-3H3,(H,27,30)(H,28,33)(H,31,32)(H2,35,36,37)/t22-,23-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

DescriptionPhosphopeptide; binds to the src SH2 domain.

N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide Dilution Calculator

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References on N-Acetyl-O-phosphono-Tyr-Glu Dipentylamide

Potent dipeptide inhibitors of the pp60c-src SH2 domain.[Pubmed:9599239]

J Med Chem. 1998 May 21;41(11):1894-908.

The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60c-src SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)2 (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

Peptide ligands of pp60(c-src) SH2 domains: a thermodynamic and structural study.[Pubmed:9174343]

Biochemistry. 1997 May 27;36(21):6283-93.

Thermodynamic measurements, structural determinations, and molecular computations were applied to a series of peptide ligands of the pp60(c-src) SH2 domain in an attempt to understand the critical binding determinants for this class of molecules. Isothermal titration calorimetry (ITC) measurements were combined with structural data derived from X-ray crystallographic studies on 12 peptide-SH2 domain complexes. The peptide ligands studied fall into two general classes: (1) dipeptides of the general framework N-acetylphosphotyrosine (or phosphotyrosine replacement)-Glu or methionine (or S-methylcysteine)-X, where X represents a hydrophobic amine, and (2) tetra- or pentapeptides of the general framework N-acetylphosphotyrosine-Glu-Glu-Ile-X, where X represents either Glu, Gln, or NH2. Dipeptide analogs which featured X as either hexanolamine or heptanolamine were able to pick up new hydrogen bonds involving their hydroxyl groups within a predominantly lipophilic surface cavity. However, due to internal strain as well as the solvent accessibility of the new hydrogen bonds formed, no net increase in binding affinity was observed. Phosphatase-resistant benzylmalonate and alpha,alpha-difluorobenzyl phosphonate analogs of phosphotyrosine retained some binding affinity for the pp60(c-src) SH2 domain but caused local structural perturbations in the phosphotyrosine-binding site. In the case where a reversible covalent thiohemiacetal was formed between a formylated phosphotyrosine analog and the thiol side chain of Cys-188, deltaS was 25.6 cal/(mol K) lower than for the nonformylated phosphotyrosine parent. Normal mode calculations show that the dramatic decrease in entropy observed for the covalent thiohemiacetal complex is due to the inability of the phosphotyrosine moiety to transform lost rotational and translational degrees of freedom into new vibrational modes.

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