structure of 2-O-(p-Nitrophenyl)-α-D-N-glycolylneuraminic Acid Methyl Ester

2-O-(p-Nitrophenyl)-α-D-N-glycolylneuraminic Acid Methyl Ester

CAS No.: 1000890-53-8
M. Wt: 460.38900
M. Fa: C18H24N2O12
InChI Key: -

Names and Identifiers of 1000890-53-8

CAS Number

1000890-53-8

IUPAC Name

methyl (2S,4S,5R,6R)-2-(4-nitrophenoxy)-4-oxidanyl-5-(2-oxidanylethanoylamino)-6-[(1R,2R)-1,2,3-tris(oxidanyl)propyl]oxane-2-carboxylate

Canonical SMILES

COC(=O)[C@]1(C[C@@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)CO)O)OC2=CC=C(C=C2)[N+](=O)[O-]

Physical and chemical properties of 1000890-53-8

Exact Mass

460.13300

Melting Point

111-113°C

Molecular Formula

C18H24N2O12

Molecular Weight

460.38900

PSA

220.83000

Solubility

Dimethyl Sulfoxide, Methanol, Water

Storage condition

Refrigerator

Applications of 1000890-53-8

The primary applications of 2-O-(p-Nitrophenyl)-alpha-D-N-glycolylneuraminic Acid Methyl Ester include:

  • Proteomics Research: Used as a substrate in studies involving glycosylation patterns.
  • Vaccine Development: Its ability to mimic sialic acids makes it useful in designing vaccines that target sialic acid-binding pathogens.
  • Drug Development: Serves as a lead compound for developing inhibitors of sialyltransferases, which are implicated in various diseases.

These applications highlight its significance in both fundamental research and applied sciences.

Interaction Studies of 1000890-53-8

Interaction studies involving 2-O-(p-Nitrophenyl)-alpha-D-N-glycolylneuraminic Acid Methyl Ester focus on its binding affinities with various proteins and enzymes:

  • Sialyltransferases: As a substrate, it provides insights into enzyme kinetics and specificity.
  • Receptors: Its interactions with sialic acid-binding receptors can elucidate mechanisms of cellular adhesion and signaling.

These studies are crucial for understanding how modifications to sialic acids can affect biological processes.

Biological Activity of 1000890-53-8

2-O-(p-Nitrophenyl)-alpha-D-N-glycolylneuraminic Acid Methyl Ester exhibits notable biological activities, particularly in the context of immunology and cell biology. It serves as a substrate for various sialyltransferases, enzymes that play crucial roles in glycoprotein synthesis. Its structural similarity to naturally occurring sialic acids allows it to interact with sialic acid-binding proteins, influencing cellular recognition processes. Additionally, this compound has been shown to modulate immune responses, making it a valuable tool in studying immune mechanisms.