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CS-W001157 4
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3-Fluoro-L-tyrosine

  • CAS No. 7423-96-3

  • Cat. No. CS-0157119
  • Purity≥97%
  • MDL No.MFCD00002607

*For research and further manufacturing use only, not for direct human use.

3-Fluoro-L-tyrosine|CS-0157119

Structure of 7423-96-3

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General Information

  • CAS No. 7423-96-3
  • Cat. No. CS-0157119
  • Purity ≥97%
  • MDL No. MFCD00002607
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀FNO₃
  • Molecular Weight 199.18
  • Synonym(s) None
  • SMILES C1=CC(=C(C=C1C[C@@H](C(=O)O)N)F)O

Description

3-Fluoro-L-tyrosine integrates a fluorinated aromatic ring into a biologically compatible amino acid scaffold, enabling site-specific incorporation into proteins via genetic code expansion. This analog supports the study of protein dynamics and structure-function relationships in live systems, offering enhanced metabolic stability and resistance to enzymatic degradation compared to native tyrosine.

Application

3-Fluoro-L-tyrosine serves as a bioisosteric analog of L-tyrosine, enabling site-specific incorporation into peptides to probe protein structure-function relationships. Its fluorinated aromatic ring enhances metabolic stability and modulates electronic properties, facilitating studies in enzyme kinetics and receptor binding. The compound exhibits excellent bench stability, tolerates standard peptide coupling conditions, and simplifies purification via its distinct chromatographic profile.

Synthesis

  • Route1

    References

    • Walker, T. E.; Matheny, C.; Storm, C. B.; Hayden, H. Journal of Organic Chemistry, 1986 , vol. 51, # 8 p. 1175 - 1179
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 120, # 28 p. 6851 - 6858
  • Route3

    References

    • Seisser, Birgit; Zinkl, Rene; Gruber, Karl; Kaufmann, Franz; Hafner, Andreas; Kroutil, Wolfgang Advanced Synthesis and Catalysis, 2010 , vol. 352, # 4 p. 731 - 736

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   83.55
  • LogP   0.4857
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   3

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