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CS-W001157 4
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Z-Tyr(tBu)-OH

  • CAS No. 5545-54-0

  • Cat. No. CS-0187718
  • Purity≥98%
  • MDL No.None

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

Z-Tyr(tBu)-OH|CS-0187718

Structure of 5545-54-0

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General Information

  • CAS No. 5545-54-0
  • Cat. No. CS-0187718
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₁H₂₅NO₅
  • Molecular Weight 371.43
  • Synonym(s) None
  • SMILES CC(C)(OC1=CC=C(C[C@H](NC(OCC2=CC=CC=C2)=O)C(O)=O)C=C1)C

Description

Z-Tyr(tBu)-OH is a protected tyrosine derivative featuring a benzyloxycarbonyl (Z) group at the N-terminus and a tert-butyl ester at the phenolic oxygen. This configuration enables selective incorporation into peptide chains during solid-phase synthesis, offering enhanced stability and reduced side reactions under standard coupling conditions.

Application

Z-Tyr(tBu)-OH serves as a protected tyrosine building block for peptide synthesis, offering stable handling and orthogonal protection. The benzyloxycarbonyl (Z) group enables selective deprotection under mild hydrogenolysis, while the tert-butyl ester facilitates efficient coupling and subsequent cleavage. This dual protection scheme supports high-yielding amide bond formation in standard solid-phase and solution-phase workflows, making Z-Tyr(tBu)-OH a reliable scaffold for synthesizing bioactive peptides and peptidomimetics.

Synthesis

  • Route1
    • null|null
      66328-78-7
    • ~89%
    • In-stock
      Z-Tyr(tBu)-OH|CS-0187718
      5545-54-0

    References

    • Lovett; Portoghese Journal of Medicinal Chemistry, 1987 , vol. 30, # 7 p. 1144 - 1149
  • Route2
    • (S)-Ethyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate|CS-0713251
      16679-94-0
    • ~%
    • In-stock
      Z-Tyr(tBu)-OH|CS-0187718
      5545-54-0

    References

    • Lovett; Portoghese Journal of Medicinal Chemistry, 1987 , vol. 30, # 7 p. 1144 - 1149
  • Route3

    References

    • Caplar, Vesna; Raza, Zlata; Katalenic, Darinka; Zinic, Mladen Croatica Chemica Acta, 2003 , vol. 76, # 1 p. 23 - 36

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

Quality Control

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Computational Chemistry Data

  • TPSA   84.86
  • LogP   3.786
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   7

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