83160
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:
Molecular Weight:
129.11
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352209
EC Number:
202-700-3
MDL number:
Beilstein/REAXYS Number:
82132
Product Name
L-Pyroglutamic acid, ≥99.0% (T)
Quality Level
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
Application
L-Pyroglutamic acid is used in the synthesis of:
It is also used in the total synthesis of (−)-stemoamide and celogentin C.
- 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.
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signalword
Danger
hcodes
Hazard Classifications
Aquatic Chronic 3 - Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Total Syntheses of (?)-and (−)-Stemoamide
Jacobi PA and Lee K
Journal of the American Chemical Society, 122(18), 4295-4303 (2000)
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)