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CS-W001157 4
Total: USD 88.00

Z-Glu(OtBu)-OH

  • CAS No. 3886-08-6

  • Cat. No. CS-W008326
  • Purity≥97%
  • MDL No.MFCD00038274

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

Z-Glu(OtBu)-OH|CS-W008326

Structure of 3886-08-6

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General Information

  • CAS No. 3886-08-6
  • Cat. No. CS-W008326
  • Purity ≥97%
  • MDL No. MFCD00038274
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₂₃NO₆
  • Molecular Weight 337.37
  • Synonym(s) None
  • SMILES O=C([C@H](CCC(OC(C)(C)C)=O)NC(OCC1=CC=CC=C1)=O)O

Description

Z-Glu(OtBu)-OH is a protected glutamic acid derivative featuring a benzyl (Z) group at the α-amino position and a tert-butyl ester at the side-chain carboxylate. This configuration enables stable incorporation into peptide synthesis workflows, offering selective protection for both amine and carboxylic acid functionalities under standard coupling conditions.

Application

Z-Glu(OtBu)-OH serves as a key chiral building block in peptide synthesis, offering stable protection of both the α-amino and side-chain carboxyl groups. The benzyloxycarbonyl (Z) group enables efficient N-terminal protection, while the tert-butyl ester facilitates selective deprotection under mild acidic conditions. Its compatibility with standard coupling reagents and robustness during multi-step sequences make it ideal for synthesizing complex peptide scaffolds and bioactive oligomers.

Synthesis

  • Route1
    • 1-Benzyl 5-(tert-butyl) ((benzyloxy)carbonyl)-L-glutamate|CS-0452192
      3967-18-8
    • ~61%
    • In-stock
      Z-Glu(OtBu)-OH|CS-W008326
      3886-08-6

    References

    • Barbayianni, Efrosini; Fotakopoulou, Irene; Schmidt, Marlen; Constantinou-Kokotou, Violetta; Bornscheuer, Uwe T.; Kokotos, George Journal of Organic Chemistry, 2005 , vol. 70, # 22 p. 8730 - 8733
  • Route2
    • null|null
      23632-68-0
    • ~83%
    • In-stock
      Z-Glu(OtBu)-OH|CS-W008326
      3886-08-6

    References

    • Chevallet, Pierre; Garrouste, Patrick; Malawska, Barbara; Martinez, Jean Tetrahedron Letters, 1993 , vol. 34, # 46 p. 7409 - 7412
  • Route3
    • null|null
      365217-97-6
    • ~88%
    • In-stock
      Z-Glu(OtBu)-OH|CS-W008326
      3886-08-6

    References

    • Fotakopoulou, Irene; Barbayianni, Efrosini; Constantinou-Kokotou, Violetta; Bornscheuer, Uwe T.; Kokotos, George Journal of Organic Chemistry, 2007 , vol. 72, # 3 p. 782 - 786

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H317-H319-H335
Precautionary Statements : P261-P264-P271-P272-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   101.93
  • LogP   2.4879
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   7

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