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CS-W001157 4
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D-Pyroglutamic acid ethyl ester

  • CAS No. 68766-96-1

  • Cat. No. CS-W002063
  • Purity≥97%
  • MDL No.MFCD00010848

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

D-Pyroglutamic acid ethyl ester|CS-W002063

Structure of 68766-96-1

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General Information

  • CAS No. 68766-96-1
  • Cat. No. CS-W002063
  • Purity ≥97%
  • MDL No. MFCD00010848
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₁NO₃
  • Molecular Weight 157.17
  • Synonym(s) Ethyl D-pyroglutamate; D-Pyroglutamic acid ethyl ester
  • SMILES CCOC(=O)[C@H]1CCC(=O)N1

Description

D-Pyroglutamic acid ethyl ester features a stable cyclic imide structure with a chiral center, offering enhanced solubility and compatibility in peptide synthesis. This bench-stable derivative simplifies incorporation into bioactive sequences, enabling efficient access to N-terminally modified peptides under standard conditions.

Application

D-Pyroglutamic acid ethyl ester serves as a versatile chiral building block for peptide and heterocyclic synthesis, offering enhanced solubility and stability compared to the free acid. Its pyroglutamyl core facilitates efficient cyclization reactions and functions as a protected form of glutamate in solid-phase peptide synthesis. The ethyl ester group enables straightforward manipulation under standard conditions, supporting broad functional group tolerance and ease of purification in multi-step sequences.

Synthesis

  • Route1
    • null|null
      64-17-5
    • In-stock
      (R)-5-Oxopyrrolidine-2-carboxylic acid|CS-W002304
      4042-36-8
    • ~99%
    • In-stock
      D-Pyroglutamic acid ethyl ester|CS-W002063
      68766-96-1

    References

    • Ibrahim, Mohamed A.; Johnson, Henry W. B.; Jeong, Joon Won; Lewis, Gary L.; Shi, Xian; Noguchi, Robin T.; Williams, Matthew; Leahy, James W.; Nuss, John M.; Woolfrey, John; Banica, Monica; Bentzien, Frauke; Chou, Yu-Chien; Gibson, Anna; Heald, Nathan; Lamb, Peter; Mattheakis, Larry; Matthews, David; Shipway, Aaron; Wu, Xiang; Zhang, Wentao; Zhou, Sihong; Shankar, Geetha Journal of Medicinal Chemistry, 2012 , vol. 55, # 3 p. 1368 - 1381
  • Route2
    • null|null
      64-17-5
    • In-stock
      D-Glutamic acid|CS-6255
      6893-26-1
    • ~87%
    • In-stock
      D-Pyroglutamic acid ethyl ester|CS-W002063
      68766-96-1

    References

    • Evans; Lundy Journal of the American Chemical Society, 1992 , vol. 114, # 4 p. 1495 - 1496
  • Route3
    • (R)-Diethyl 2-aminopentanedioate|CS-0497967
      13107-55-6
    • ~%
    • In-stock
      D-Pyroglutamic acid ethyl ester|CS-W002063
      68766-96-1

    References

    • Hamada; Hara; Kawai; Kohno; Shioiri Tetrahedron, 1991 , vol. 47, # 40 p. 8635 - 8652

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   55.4
  • LogP   -0.1719
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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