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A8625

Sigma-Aldrich

N-Acetil-D-glucosamina

≥99% (HPLC)

Sinónimos:

2-Acetamido-2-desoxi-D-glucosa, D-GlcNAc

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About This Item

Fórmula empírica (notación de Hill):
C8H15NO6
Número de CAS:
7512-17-6
Peso molecular:
221.21
Beilstein:
1727589
Número CE:
231-368-2
Número MDL:
MFCD00061615
Código UNSPSC:
12352201
ID de la sustancia en PubChem:
24891348
NACRES:
NA.25
En este momento no podemos mostrarle ni los precios ni la disponibilidad

origen biológico

crab (red)

Nivel de calidad

200

Ensayo

≥99% (HPLC)

Formulario

powder

técnicas

HPLC: suitable

color

white to off-white

mp

211 °C (dec.) (lit.)

solubilidad

H2O: 50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)

temp. de almacenamiento

−20°C

cadena SMILES

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8?/m1/s1

Clave InChI

OVRNDRQMDRJTHS-RTRLPJTCSA-N

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Descripción general

La N-acetilglucosamina (GlcNAc) es el derivado acetilado de la glucosamina (GlcN). Es un componente importante de los proteoglucanos, las glucoproteínas, los glucosaminoglucanos (GAG) y otras unidades estructurales que se encuentran en el tejido conjuntivo.

Aplicación

La N-acetil-D-glucosamina se ha utilizado:
  • como azúcar para la inhibición competitiva en histoquímica con lectinas
  • como componente en el medio Barbour-Stonner-Kelly (BSK) para cultivar cepas de las espiroquetas Borrelia burgdorferi
  • como componente del tampón de unión para suspender cepas de Streptococcus pneumoniae destinado al ensayo de inhibición para examinar la especificidad de unión de la ficolina M a cepas de S. pneumoniae

Acciones bioquímicas o fisiológicas

La N-acetilglucosamina (GlcNAc) se utiliza principalmente en las industrias alimentaria, cosmética y farmacéutica.

Otras notas

Si desea conocer por completo nuestra amplia gama de monosacáridos para su investigación, le recomendamos que visite nuestra página de categoría Carbohidratos .

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

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000427618
0000422065
0000422064
0000422064
0000422065

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Visite la Librería de documentos

Colette Cywes-Bentley et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(24), E2209-E2218 (2013-05-30)
Microbial capsular antigens are effective vaccines but are chemically and immunologically diverse, resulting in a major barrier to their use against multiple pathogens. A β-(1→6)-linked poly-N-acetyl-d-glucosamine (PNAG) surface capsule is synthesized by four proteins encoded in genetic loci designated intercellular
Lucy G Weaver et al.
Carbohydrate research, 371, 68-76 (2013-03-26)
Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the
Mikkel Girke Jørgensen et al.
Genes & development, 27(10), 1132-1145 (2013-05-15)
Many bacterial small RNAs (sRNAs) regulate gene expression through base-pairing with mRNAs, and it has been assumed that these sRNAs act solely by this one mechanism. Here we report that the multicellular adhesive (McaS) sRNA of Escherichia coli uniquely acts
Gerald W Hart et al.
Nature, 446(7139), 1017-1022 (2007-04-27)
All animals and plants dynamically attach and remove O-linked beta-N-acetylglucosamine (O-GlcNAc) at serine and threonine residues on myriad nuclear and cytoplasmic proteins. O-GlcNAc cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a
Jason M Berk et al.
The Journal of biological chemistry, 288(42), 30192-30209 (2013-09-10)
Emerin, a membrane component of nuclear "lamina" networks with lamins and barrier to autointegration factor (BAF), is highly O-GlcNAc-modified ("O-GlcNAcylated") in mammalian cells. Mass spectrometry analysis revealed eight sites of O-GlcNAcylation, including Ser-53, Ser-54, Ser-87, Ser-171, and Ser-173. Emerin O-GlcNAcylation
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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. What is the physicochemical method or principle used to determine optical rotation in this product, could you confirm that the product is released with polarimetry?

    1 answer

    1. The method of analysis for this product is considered proprietary, however details and conditions are published in the Certificate of Analysis. See the link below for a sample CofA.
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/A8625-5G0000185218.pdf

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