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Chemical Structure| 3849-21-6 Chemical Structure| 3849-21-6
Chemical Structure| 3849-21-6

Ethyl 2-cyano-2-(hydroxyimino)acetate

CAS No.: 3849-21-6

4.5 *For Research Use Only !

Cat. No.: A671796 Purity: 95%

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Product Citations

Product Citations

Calabretta, Lindsey O. ; Yang, Jinyi ; Raines, Ronald T. ;

Abstract: The field of cell-penetrating peptides is dominated by the use of oligomers of arginine residues. Octanol-water partitioning in the presence of an anionic lipid is a validated proxy for cell-penetrative efficacy. Here, we add one, two, or three N-Me groups to Ac-Arg-NH2 and examine the effects on octanol-water partitioning. In the absence of an anionic lipid, none of these arginine derivatives can be detected in the octanol layer. In the presence of sodium dodecanoate, however, increasing N-methylation correlates with increasing partitioning into octanol, which is predictive of higher cell-penetrative ability. We then evaluated fully Nα-methylated oligoarginine peptides and observed an increase in their cellular penetration compared with canonical oligoarginine peptides in some contexts. These findings indicate that a simple modification, Nα-methylation, can enhance the performance of cell-penetrating peptides.

Keywords: guanidino group ; octanol-water partitioning ; peptoid ; topological polar surface area

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Product Details of Ethyl 2-cyano-2-(hydroxyimino)acetate

CAS No. :3849-21-6
Formula : C5H6N2O3
M.W : 142.11
SMILES Code : O=C(C(C#N)=NO)OCC
MDL No. :MFCD00002112

Safety of Ethyl 2-cyano-2-(hydroxyimino)acetate

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H301-H317-H319
Precautionary Statements:P210-P240-P264-P270-P280-P301+P310-P330-P370+P378-P403+P233-P405-P501
Class:4.1(6.1)
UN#:2926
Packing Group:

Application In Synthesis of Ethyl 2-cyano-2-(hydroxyimino)acetate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 3849-21-6 ]
  • Downstream synthetic route of [ 3849-21-6 ]

[ 3849-21-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 3849-21-6 ]
  • [ 37842-58-3 ]
References: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 441 - 451.
[2] Chemistry - A European Journal, 2015, vol. 21, # 16, p. 6090 - 6099.
 

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