N-Glycolylneuraminic Acid（Neu5Gc） - ≥95%(HPLC) , CAS No.1113-83-3

CAS: 1113-83-3 Cat. No.: G115995 Molecular Weight: 325.27 Beilstein Registry Number: 1716828

GRADE & PURITY ≥95%(HPLC)

Synonyms

Neu5Glc | NeuNGl

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

N-Glycolylneuraminic acid (Neu5Gc) is the most common sialic acid formed as a result of the hydroxylation of the methyl group of the 5-N-acetyl moiety of N-acetylneuraminic acid (Neu5Ac). It is predominantly found in sea urchins and starfish and is broadly distributed in glycoproteins and gangliosides of sperm cells and oocyte. Neu5Gc belongs to the family of Sia.

Product Application

N-Glycolylneuraminic acid has been used:
①as a sugar in microtiter biofilm methodologic approach for the enhancement of biofilm formation.
②as a standard for the determination of sialic acids in the nervous system of silkworm and to find the variations of sialic acids among different developmental stages.
③as a standard in the high-performance liquid chromatography (HPLC) analyses to detect the molecular species of sialic acid (Sia) species using 1,2-diamino-4,5-methylenedioxy-benzene (DMB) as a fluorogenic compound.

Specifications

Synonyms

Neu5Glc | NeuNGl

Specifications & Purity

≥95%(HPLC)

Biochemical and Physiological Mechanisms

N-glycolylneuraminic acid (Neu5Gc) is the hydroxylated form of the commonly known sialic acid N-acetylneuraminic acid (Neu5Ac). This compound is biosynthesized through the activity of cytidine monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac) hydroxylase

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%(HPLC)

Names and Identifiers

• Canonical Smiles: C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)NC(=O)CO)O
• IUPAC Name: (2S,4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• InChIKey: FDJKUWYYUZCUJX-AJKRCSPLSA-N
• INCHI: 1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H](O[C@@]1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O
• WGK Germany: 3
• Molecular Weight: 325.27
• Beilstein: 1716828
• Reaxy-Rn: 37819147
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37819147&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Sugar acids and derivatives
          • Level6 Sugar amino acids and derivatives
            • Level7 Pyranoid amino acids and derivatives
              • Level8 Neuraminic acids and derivatives
                • Level9 Neuraminic acids

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Sugar acids and derivatives - Sugar amino acids and derivatives - Pyranoid amino acids and derivatives - Neuraminic acids and derivatives
• Direct Parent: Neuraminic acids
• Alternative Parents: C-glucuronides C-glycosyl compounds Pyrans Alpha hydroxy acids and derivatives Oxanes Secondary alcohols Hemiacetals Propargyl-type 1,3-dipolar organic compounds Polyols Carboximidic acids Carboxylic acids Oxacyclic compounds Monocarboxylic acids and derivatives Primary alcohols Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Neuraminic acid - C-glucuronide - C-glycosyl compound - Glycosyl compound - Alpha-hydroxy acid - Hydroxy acid - Oxane - Pyran - Hemiacetal - Secondary alcohol - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Carboxylic acid - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Polyol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Alcohol - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Primary alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.
• External Descriptors: N-acylneuraminic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat sensitive
• Molecular Weight: 325.270 g/mol
• XLogP3: -4.100
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 325.101 Da
• Monoisotopic Mass: 325.101 Da
• Topological Polar Surface Area: 197.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 418.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Enqi He, Wei Quan, Jie Luo, Chuxin Liu, Wanting Zheng, Qingwu Shen.  (2023)  Absorption and Transport Mechanism of Red Meat-Derived N-glycolylneuraminic Acid and Its Damage to Intestinal Barrier Function through the NF-κB Signaling Pathway.  Toxins,  15  (2): (132).  [PMID:36828446] [10.3390/toxins15020132]

2. Zhang Xin, Wang Chen, Han Qing, Chen Xuan, Li Guoyun, Yu Guangli.  (2021)  Highly sialylated mucin-type glycopeptide from porcine intestinal mucosa after heparin extraction: O-glycan profiling and immunological activity evaluation.  GLYCOCONJUGATE JOURNAL,  38  (5): (527-537).  [PMID:34480673] [10.1007/s10719-021-10014-y]

3. Yue Wu, Huiling Zhou, Yuxin Liu, Ling Wang, Feng Gao, Qicai Liu.  (2024)  Neu5Gc regulates decidual macrophages leading to abnormal embryo implantation.  GENES AND IMMUNITY,      [PMID:38499667] [10.1038/s41435-024-00268-5]

4. Su Fang, Jianrong Wu, Wenxuan Niu, Tiantian Zhang, Tiantian Hong, Hongtao Zhang, Xiaobei Zhan.  (2024)  Sialylation of dietary mucin modulate its digestibility and the gut microbiota of elderly individuals.  FOOD RESEARCH INTERNATIONAL,      [PMID:38609225] [10.1016/j.foodres.2024.114246]

5. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang.  (2024)  The global phosphorylation landscape of mouse oocytes during meiotic maturation.  EMBO JOURNAL,      [PMID:39256562] [10.1038/s44318-024-00222-1]

6. Qianyun Fu, Guoyun Li, Chen Wang, Ya Wang, Qinying Li, Jiejie Hao, Guangli Yu.  (2019)  Profiling and Structural Characterization of High Neu5Gc or Sulfate-Containing O-glycans from Hyla Rabbit Intestinal Mucin.  MOLECULES,  24  (7): (1365).  [PMID:30959980] [10.3390/molecules24071365]

7. Zhaoyi Zhang, Xuefei Shao, Sam Al-Dalali, Baocai Xu, Peijun Li.  (2025)  Distinct mechanisms of N-glycolylneuraminic acid reduction by Lactiplantibacillus plantarum R2 and Staphylococcus carnosus C1: Adsorption versus biodegradation.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107937]

8. Peng Zhuang, Gao Yang, Zhang Xinrui, Yang Huiyu, Su Bo, Li Kai, Zhang Cunlin.  (2025)  Analysis on the terahertz spectral characteristics of two types of sialic acids in solid state and aqueous solution.  Scientific Reports,  15  (1): (42783).  [PMID:41315791] [10.1038/s41598-025-26912-2]