UDP-GalNAc

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Molecular Weight

651.32

Formula

C17H25N3Na2O17P2

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O[C@H]1[C@H](N2C(NC(C=C2)=O)=O)O[C@H](COP(OP(O[C@@H]3[C@@H]([C@H]([C@H](O)[C@@H](CO)O3)O)NC(C)=O)(O[Na])=O)(O[Na])=O)[C@H]1O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

-20°C, sealed storage, away from moisture

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UDP-GalNAc (Uridine Diphosphate N-Acetylgalactosamine) is a nucleotide sugar involved in the biosynthesis of glycoproteins and glycolipids. It consists of uridine diphosphate (UDP) linked to N-acetylgalactosamine (GalNAc), a derivative of the monosaccharide galactose modified with an acetyl group. UDP-GalNAc plays a crucial role in glycosylation processes across many biological systems.

Structure & Properties:

  • Molecular Weight (MW): Approximately 606 g/mol
  • Chemical Formula: C17H27N3O17P2
  • Synonyms: UDP-N-acetylgalactosamine
  • Functional Groups: The N-acetylgalactosamine group is characterized by the acetylation of an amino group (-NH2) at the 2-position of the galactose sugar ring, making it an amino sugar.

Biological Role:

  • Biosynthesis Pathway: UDP-GalNAc is synthesized in the cytoplasm of cells through enzymatic pathways that convert UDP-glucose into UDP-GalNAc. It serves as a sugar donor in the glycosylation of proteins and lipids.
  • Function: UDP-GalNAc transfers N-acetylgalactosamine to serine or threonine residues on proteins, forming O-linked glycans. It is also involved in the biosynthesis of glycosphingolipids.

Applications:

  • O-Glycosylation: UDP-GalNAc is the primary substrate for the initiation of O-glycosylation, a post-translational modification where sugars are added to proteins, particularly on mucins.
  • Glycosphingolipid Biosynthesis: It plays a role in the formation of complex glycosphingolipids, which are important for cell membrane structure and signaling.

Significance in Research:

  • Cell Signaling and Adhesion: The glycoconjugates formed with UDP-GalNAc are involved in cell signaling, cellular adhesion, and immune recognition, which makes them significant in studies of cancer, inflammation, and infectious diseases.
  • Disease Association: Disruptions in UDP-GalNAc metabolism or glycosylation processes can lead to diseases such as congenital disorders of glycosylation (CDG).

Key Roles:

  • O-Glycan Biosynthesis: UDP-GalNAc is responsible for the biosynthesis of O-glycans, particularly in the formation of mucins, which protect epithelial surfaces.
  • Glycolipid Biosynthesis: It is also involved in synthesizing glycosphingolipids, which are essential for cell membrane stability and function.

Storage and Stability:

  • Storage: UDP-GalNAc should be stored at -20°C in a moisture-free environment.
  • Stability: The compound is stable under these conditions but may degrade when exposed to heat, moisture, or light.

Research Applications:

  • Glycobiology: UDP-GalNAc is widely used in research to study glycosylation processes and the role of O-glycans in cellular biology.
  • Therapeutic Development: The understanding of UDP-GalNAc in glycosylation can lead to potential therapeutic strategies, particularly for glycosylation-related diseases.

Potential Impact:

  • Cancer Therapy: Abnormal O-glycosylation patterns are often seen in cancer cells, and targeting the enzymes that use UDP-GalNAc could offer new therapeutic approaches.
  • Synthetic Biology: UDP-GalNAc can be used in synthetic biology to engineer glycan structures for therapeutic and diagnostic purposes.

Key Research Areas:

  • Mucins and Immune Response: Researching the role of UDP-GalNAc in the biosynthesis of mucins, which are important in immune defense, is critical for understanding diseases of the mucosal surfaces.
  • Glycosylation Disorders: Investigating the metabolism of UDP-GalNAc may provide insights into congenital disorders of glycosylation and other metabolic diseases.

Conclusion:

UDP-GalNAc is a fundamental sugar nucleotide involved in critical biological processes such as O-glycosylation and glycolipid biosynthesis. Its role in cellular communication, immune responses, and disease pathology makes it a key molecule in glycobiology research and therapeutic development.

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Size

15 MG, 25 MG, 5 MG

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