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83160

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
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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.[1]
  • Chiral N-heterocyclic carbenes (NHCs) as catalysts for the asymmetric dimerization of alkylarylketenes to give the corresponding α-quaternary β-alkylidenyl-β-lactones.[2]

It is also used in the total synthesis of (−)-stemoamide[3] and celogentin C.[4]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6412
BCCJ8845
BCCG8513
BCCF4459
BCCD8715

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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)
Franz Gruber et al.
Current biology : CB, 23(6), 507-514 (2013-03-13)
Motivation controls behavior [1]. A variety of food-related behaviors undergo motivational modulation by hunger, satiety, and other states [2-4]. Here we searched for critical satiation factors modulating approach to an odor associated with sugar reward in Drosophila melanogaster. We selectively
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. Is this food grade?

    1 answer

    1. This item is not a food grade product. Currently, a food grade L-Pyroglutamic acid is not available.

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