Methyl L-pyroglutamate

Name: Methyl L-pyroglutamate
Brand: ChemScene
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CAS No. 4931-66-2
Cat. No. CS-D0637
Molecule weight143.14
Purity≥97%
MDL No.MFCD00080931

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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General Information

CAS No. 4931-66-2
Cat. No. CS-D0637
Purity ≥97%
MDL No. MFCD00080931
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₉NO₃
Molecular Weight 143.14
Synonym(s) (S)-Methyl 5-oxopyrrolidine-2-carboxylate; L-Pyroglutamic acid methyl ester
SMILES O=C(OC)[C@H](CC1)NC1=O

Description

Methyl L-pyroglutamate delivers a stable, bioactive pyroglutamate scaffold ideal for peptide synthesis and medicinal chemistry applications. This bench-stable derivative features a cyclic lactam structure that enhances conformational rigidity, improving target binding affinity in peptidomimetic designs. Its solubility profile supports efficient incorporation into diverse synthetic workflows.

Application

Methyl L-pyroglutamate serves as a stable, bench-ready building block for the synthesis of bioactive peptides and heterocyclic scaffolds. Its cyclic imide structure provides enhanced stability and predictable reactivity in amide bond formation and nucleophilic substitution reactions. The methyl ester group enables straightforward derivatization, while the protected pyrrolidine core offers compatibility with diverse synthetic transformations, facilitating efficient access to complex molecular architectures.

Synthesis

Route1
- In-stock
  
  98-79-3
- ~94%
- In-stock
  
  4931-66-2
References
- Abbott Laboratories Patent: US5516912 A1, 1996 ;
Route2
- 67-56-1
- In-stock
  
  98-79-3
- ~97%
- In-stock
  
  4931-66-2
References
- Brena-Valle; Cruz-Almanza; Guadarrama-Morales Synthetic Communications, 2001 , vol. 31, # 5 p. 697 - 706
Route3
- 67-56-1
- In-stock
  
  149-87-1
- ~%
- In-stock
  
  4931-66-2
References
- Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R. Patent: US2005/65178 A1, 2005 ; Location in patent: Page/Page column 17 ;

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 -0.562
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Glutamic acid and derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Amino Acid Derivatives

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Biochemistry Biochemicals and Reagents Amino Acids C-ProtectedAmino Acids

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Methyl L-pyroglutamate

CAS No. 4931-66-2

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