83160

L-Pyroglutamic acid

≥99.0% (T), for peptide synthesis

• Synonym(s): (S)-(−)-2-Pyrrolidone-5-carboxylic acid, (S)-5-Oxo-2-pyrrolidinecarboxylic acid
• Empirical Formula (Hill Notation): C₅H₇NO₃
• CAS Number: 98-79-3
• Molecular Weight: 129.11
• Beilstein/REAXYS Number: 82132
• EC Number: 202-700-3
• MDL number: MFCD00005272
• UNSPSC Code: 12352209
• PubChem Substance ID: 57652948
• NACRES: NA.22

Properties

• product name: L-Pyroglutamic acid, ≥99.0% (T)
• assay: ≥99.0% (T)
• form: solid
• optical activity: [α]20/D −10.5±1°, c = 5% in H₂O
• optical purity: enantiomeric ratio: ≥99:1 (GC)
• reaction suitability: reaction type: solution phase peptide synthesis
• ign. residue: ≤0.05%
• mp: 155-162 °C; 160-163 °C (lit.)
• application(s): peptide synthesis
• SMILES string: OC(=O)[C@@H]1CCC(=O)N1
• InChI: 1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
• InChI key: ODHCTXKNWHHXJC-VKHMYHEASA-N

Description

Application

L-Pyroglutamic acid is used in the synthesis of:

• Nonproteinogenic amino acids such as (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and (3S,4R)-3,4-dimethyl-L-glutamine.
• Chiral N-heterocyclic carbenes (NHCs) as catalysts for the asymmetric dimerization of alkylarylketenes to give the corresponding α-quaternary β-alkylidenyl-β-lactones.

It is also used in the total synthesis of (−)-stemoamide and celogentin C.

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H318,H412
• pcodes: P273 - P280 - P305 + P351 + P338 - P501
• Hazard Classifications: Aquatic Chronic 3 - Eye Dam. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves