Date published: 2025-10-17

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Woodward′s reagent K (CAS 4156-16-5)

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Alternate Names:
2-Ethyl-5-phenylisoxazolium-3′-sulfonate; NEPIS
Application:
Woodward′s reagent K is a coupling reagent for peptide synthesis
CAS Number:
4156-16-5
Purity:
≥95%
Molecular Weight:
253.27
Molecular Formula:
C11H11NO4S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Ethyl-5-phenylisoxazolium-3′-sulfonate (Woodward′s reagent K) is a compound of interest within the field of chemical biology for its role as a reagent in the modification of nucleic acids. It is utilized in the study of RNA and DNA by targeting specific nucleotide sequences, enabling researchers to investigate the structure and function of nucleic acids. This compound′s reactivity with anionic sites on nucleotides provides insights into the mechanisms of nucleic acid interactions and stability. Furthermore, 2-Ethyl-5-phenylisoxazolium-3′-sulfonate is used in the development of novel biochemical assays that monitor the activity of enzymes, like nucleases and polymerases, that act upon nucleic acids. In addition, its use in probing the binding sites of nucleic acid-binding proteins helps in elucidating the complex network of biomolecular interactions.


Woodward′s reagent K (CAS 4156-16-5) References

  1. Inhibitory effects of Woodward's reagent K on carrier-mediated anion transport in rabbit intestinal brush border membrane vesicles.  |  Tam, TN. and Schron, CM. 1999. Zhonghua Yi Xue Za Zhi (Taipei). 62: 98-106. PMID: 10063720
  2. Spectrophotometric tool for the determination of the total carboxylate content in proteins; molar extinction coefficient of the enol ester from Woodward's reagent K reacted with protein carboxylates.  |  Kosters, HA. and de Jongh, HH. 2003. Anal Chem. 75: 2512-6. PMID: 12918999
  3. The myth of coupling reagents.  |  Bodanszky, M. 1992. Pept Res. 5: 134-9. PMID: 1421800
  4. Inactivation of human liver arginase by Woodward's reagent K: evidence for reaction with His141.  |  Carvajal, N., et al. 2004. Protein J. 23: 179-83. PMID: 15200049
  5. Direct electron transfer enhancement of covalently bound tyrosinase to glassy carbon via Woodward's reagent K.  |  Faridnouri, H., et al. 2011. Bioelectrochemistry. 82: 1-9. PMID: 21715233
  6. Gas-Phase Amidation of Carboxylic Acids with Woodward's Reagent K Ions.  |  Peng, Z., et al. 2015. J Am Soc Mass Spectrom. 26: 1686-94. PMID: 26122523
  7. Activity-Based Proteome Profiling Probes Based on Woodward's Reagent K with Distinct Target Selectivity.  |  Qian, Y., et al. 2016. Angew Chem Int Ed Engl. 55: 7766-71. PMID: 27159346
  8. Covalent Protein Labeling at Glutamic Acids.  |  Martín-Gago, P., et al. 2017. Cell Chem Biol. 24: 589-597.e5. PMID: 28434875
  9. Conversion of Woodward's Reagent K in an aqueous medium: mathematical analysis applied to enzyme modification.  |  Kuimov, AN. and Kochetov, GA. 1988. Anal Biochem. 172: 56-60. PMID: 3189775
  10. Woodward's reagent K inactivation of Escherichia coli L-threonine dehydrogenase: increased absorbance at 340-350 nm is due to modification of cysteine and histidine residues, not aspartate or glutamate carboxyl groups.  |  Johnson, AR. and Dekker, EE. 1996. Protein Sci. 5: 382-90. PMID: 8745417
  11. A novel method for chemical modification of functional groups other than a carboxyl group in proteins by N-ethyl-5-phenylisooxazolium-3'-sulfonate (Woodward's reagent-K): inhibition of ADP-induced platelet responses involves covalent modification of aggregin, an ADP receptor.  |  Puri, RN. and Colman, RW. 1996. Anal Biochem. 240: 251-61. PMID: 8811919
  12. Woodward's reagent K reacts with histidine and cysteine residues in Escherichia coli and Saccharomyces cerevisiae phosphoenolpyruvate carboxykinases.  |  Bustos, P., et al. 1996. J Protein Chem. 15: 467-72. PMID: 8895092
  13. Mechanism of acylphosphatase inactivation by Woodward's reagent K.  |  Paoli, P., et al. 1997. Biochem J. 328 (Pt 3): 855-61. PMID: 9396731

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Woodward′s reagent K, 1 g

sc-251746
1 g
$311.00