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83160

L-Pyroglutamic acid

Name: <SC>L</SC>-Pyroglutamic acid
Brand: ALDRICH

≥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

NACRES:

NA.22

PubChem Substance ID:

57652948

UNSPSC Code:

12352209

EC Number:

202-700-3

MDL number:

MFCD00005272

Beilstein/REAXYS Number:

82132

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Product Name

L-Pyroglutamic acid, ≥99.0% (T)

Quality Level

200

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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Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

Building Blocks, Resins, and Coupling Reagents for GLP-1 Synthesis

Chemistry & Biochemicals

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

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)

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)

Relationship of dimethylglycine, choline, and betaine with oxoproline in plasma of pregnant women and their newborn infants.

Russell W Friesen et al.

The Journal of nutrition, 137(12), 2641-2646 (2007-11-22)

Choline and glycine are inter-related through their roles in methyl metabolism. Choline is metabolized to betaine, which donates a methyl group to homocysteine to form methionine, also generating dimethylglycine, which is further metabolized to glycine. Choline is transported across the

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Global Trade Item Number

SKU	GTIN
CDS018107-10MG	04061828981373
83160-500G	04061832596501
83160-100G	04061833005422
83160-25G	04061833005439

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