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Sigma-Aldrich

L-Pyroglutamic acid

≥99.0% (T), for peptide synthesis

Synonym(s):

(S)-(−)-2-Pyrrolidone-5-carboxylic acid, (S)-5-Oxo-2-pyrrolidinecarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H7NO3
CAS Number:
98-79-3
Molecular Weight:
129.11
Beilstein:
82132
EC Number:
202-700-3
MDL number:
MFCD00005272
UNSPSC Code:
12352209
PubChem Substance ID:
57652948
NACRES:
NA.22

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

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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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Asymmetric Dimerization of Disubstituted Ketenes Catalyzed by N-Heterocyclic Carbenes
Lv H and Zhang et al.
advanced synthesis and catalysis, 350(17), 2715-2718 (2008)
Total Synthesis of Celogentin C by Stereoselective C-H Activation
Feng Y and Chen G
Angewandte Chemie (International ed. in English), 122(5), 970-973 (2010)
Synthesis and analysis of the sterically constrained L-glutamine analogues (3S, 4R)-3, 4-dimethyl-L-glutamine and (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid
Acevedo CM et al.
Tetrahedron, 57(30), 6353-6359 (2001)
Total Syntheses of (?)-and (−)-Stemoamide
Jacobi PA and Lee K
Journal of the American Chemical Society, 122(18), 4295-4303 (2000)
Andrea Bednářová et al.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology, 164(1), 91-100 (2012-10-23)
Glucagon is conventionally regarded as a hormone, counter regulatory in function to insulin and plays a critical anti-hypoglycemic role by maintaining glucose homeostasis in both animals and humans. Glucagon performs this function by increasing hepatic glucose output to the blood
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