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649694

Sigma-Aldrich

N-Acetyl-D-neuraminic acid-1,2,3-13C3

≥99 atom % 13C, ≥97% (CP)

Synonym(s):

Sialic-13C3 acid

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About This Item

Empirical Formula (Hill Notation):
13C3C8H19NO9
CAS Number:
1172608-56-8
Molecular Weight:
312.25
MDL number:
MFCD08459893
UNSPSC Code:
12352005
PubChem Substance ID:
329760017
NACRES:
NA.12

isotopic purity

≥99 atom % 13C

Quality Level

200

Assay

≥97% (CP)

mp

186 °C (lit.)

mass shift

M+3

storage temp.

−20°C

SMILES string

CC(=O)N[C@@H]1[C@@H](O)[13CH2][13C](O)(O[C@H]1[C@H](O)[C@H](O)CO)[13C](O)=O

InChI

1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11?/m0/s1/i2+1,10+1,11+1

InChI key

SQVRNKJHWKZAKO-JQVNYIDJSA-N

General description

N-Acetyl-D-neuraminic acid-1,2,3-13C3 is an isotope analog of N-Acetyl-D-neuraminic acid.

Application

N-Acetyl-D-neuraminic acid-1,2,3-13C3 can be used to quantify acyclic keto, keto hydrate, and enol forms by 13C NMR spectroscopy. It is also used to determine sialic acid supplementation as a therapeutic avenue for NANS-deficient patients.

Packaging

This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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D-(+)-Galactose ≥99% (HPLC)

Sigma-Aldrich

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Thomas Klepach et al.
Journal of the American Chemical Society, 130(36), 11892-11900 (2008-08-20)
Aqueous solutions of N-acetyl-neuraminic acid (Neu5Ac, 1) labeled with (13)C at C1, C2, and/or C3 were analyzed by (13)C NMR spectroscopy to detect and quantify the acyclic forms (keto, keto hydrate, enol) present at varying pHs. In addition to pyranoses
Mark D Jankowski et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 238, 110336-110336 (2019-09-03)
Understanding variation in physiological traits across taxa is a central question in evolutionary biology that has wide-ranging implications in biomedicine, disease ecology, and environmental protection. Sialic acid (Sia), and in particular, 5-N-acetylneuraminic acid (Neu5Ac), is chemically bound to galactose and
Lilian Dubois et al.
Journal of medicinal chemistry, 63(15), 8231-8249 (2020-07-02)
Sialin, encoded by the SLC17A5 gene, is a lysosomal sialic acid transporter defective in Salla disease, a rare inherited leukodystrophy. It also enables metabolic incorporation of exogenous sialic acids, leading to autoantibodies against N-glycolylneuraminic acid in humans. Here, we identified
Christel Tran et al.
Molecular genetics and metabolism reports, 28, 100777-100777 (2021-07-15)
In NANS deficiency, biallelic mutations in the N-acetylneuraminic acid synthase (NANS) gene impair the endogenous synthesis of sialic acid (N-acetylneuraminic acid) leading to accumulation of the precursor, N-acetyl mannosamine (ManNAc), and to a multisystemic disorder with intellectual disability. The aim

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