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Merck

83160

Sigma-Aldrich

L-Pyroglutamic acid

≥99.0% (T), for peptide synthesis

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C5H7NO3
Número de CAS:
Peso molecular:
129.11
Beilstein:
82132
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nombre del producto

L-Pyroglutamic acid, ≥99.0% (T)

Ensayo

≥99.0% (T)

Formulario

solid

actividad óptica

[α]20/D −10.5±1°, c = 5% in H2O

pureza óptica

enantiomeric ratio: ≥99:1 (GC)

idoneidad de la reacción

reaction type: solution phase peptide synthesis

residuo de ign.

≤0.05%

mp

155-162 °C
160-163 °C (lit.)

aplicaciones

peptide synthesis

cadena SMILES

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

Clave InChI

ODHCTXKNWHHXJC-VKHMYHEASA-N

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Aplicación

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]

Pictogramas

Corrosion

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Aquatic Chronic 3 - Eye Dam. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Visite la Librería de documentos

Total Syntheses of (?)-and (−)-Stemoamide
Jacobi PA and Lee K
Journal of the American Chemical Society, 122(18), 4295-4303 (2000)
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 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)
M H Creer et al.
Clinical chemistry, 35(4), 684-686 (1989-04-01)
Pyroglutamic acidemia, a rare metabolic disorder, usually appears in infancy. It is characterized by retardation, ataxia, hemolytic anemia, and chronic acidosis and is caused by a marked deficiency of glutathione synthetase (EC 6.3.2.3) activity. This disease is inherited as an

Protocolos

Science Slam panel: Leading gene therapy developers discuss commercialization challenges and the importance of robust process development plans.

Science Slam panel: Leading gene therapy developers discuss commercialization challenges and the importance of robust process development plans.

Science Slam panel: Leading gene therapy developers discuss commercialization challenges and the importance of robust process development plans.

Science Slam panel: Leading gene therapy developers discuss commercialization challenges and the importance of robust process development plans.

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

      Helpful?

  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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