2-Acetamido-2-deoxy-d-glucono-(1,5)-lactone (also known as N-acetylglucosamine lactone) is a naturally occurring compound found in various biological systems. It is a derivative of N-acetylglucosamine (GlcNAc), a key component of chitin and glycoproteins. This lactone form of GlcNAc is of particular interest due to its unique properties and potential applications.
**Synthesis:**
The compound can be synthesized through various chemical methods, often starting from D-glucosamine or GlcNAc. One common method involves the oxidation of GlcNAc followed by lactonization.
**Effects:**
2-Acetamido-2-deoxy-d-glucono-(1,5)-lactone has been shown to exhibit various biological effects, including:
* **Anti-inflammatory activity:** Studies have suggested that this compound can inhibit the production of pro-inflammatory cytokines.
* **Anti-cancer properties:** Some research indicates that it may have anti-proliferative effects on certain cancer cells.
* **Immunomodulatory effects:** It can modulate the immune system, potentially influencing the response to pathogens and autoimmune diseases.
**Importance and Research:**
The importance of this compound lies in its potential therapeutic applications. Researchers are actively exploring its role in:
* **Drug development:** Its biological activities make it a promising candidate for developing new medications for various diseases.
* **Biocompatible materials:** Its biocompatibility and structural properties make it suitable for use in biomaterials and drug delivery systems.
* **Glycoscience research:** Understanding its structure and interactions with biological systems contributes to the advancement of glycoscience.
**Why it is studied:**
2-Acetamido-2-deoxy-d-glucono-(1,5)-lactone is studied because of its potential as a therapeutic agent and its role in various biological processes. Researchers aim to gain a comprehensive understanding of its biological properties and potential applications in medicine and biomaterials.'
| ID Source | ID |
|---|---|
| PubMed CID | 87901 |
| SCHEMBL ID | 657716 |
| MeSH ID | M0081309 |
| Synonym |
|---|
| 2-acetamido-2-deoxy-d-glucono-1,5-lactone |
| DB02813 |
| n-acetylglucosaminolactone |
| 2-(acetylamido)-2-deoxy-d-glucono-1,5-lactone |
| 19026-22-3 |
| n-[(3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxooxan-3-yl]acetamide |
| 2-acetamido-2-deoxy-1,5-gluconolactone |
| cd-80110 |
| unii-09ici1v6ax |
| einecs 242-761-3 |
| 09ici1v6ax , |
| 2-acetamido-2-deoxy-d-glucono-(1,5)-lactone |
| cd 80110 |
| 2-acetamido-2-deoxy-d-gluconolactone |
| SCHEMBL657716 |
| 2XSB |
| W-201698 |
| n-[(3r,4r,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-oxotetrahydro-2h-pyran-3-yl]acetamide (non-preferred name) |
| Q27093770 |
| d-gluconic acid, 2-(acetylamino)-2-deoxy-, delta-lactone |
| d-gluconic acid, 2-(acetylamino)-2-deoxy-, .delta.-lactone |
| n-acetylglucosamino-1,5-lactone |
| DTXSID501291445 |
| PD007618 |
| Role | Description |
|---|---|
| pheromone | A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. |
| EC 2.3.2.52 (beta-N-acetylhexosaminidase) inhibitor | An EC 2.3.2.* (aminoacyltransferase) inhibitor that interferes with the action of beta-N-acetylhexosaminidase (EC 2.3.2.52). |
| animal metabolite | Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| deoxygluconolactone | An aldonolactone derived from glucose with one or more of the hydroxy groups replaced by hydrogen. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Hyaluronoglucosaminidase | Oceanicola granulosus HTCC2516 | IC50 (µMol) | 11.0000 | 11.0000 | 11.0000 | 11.0000 | AID977608 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID977608 | Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB | 2010 | The Biochemical journal, Nov-15, Volume: 432, Issue:1 | Human OGA binds substrates in a conserved peptide recognition groove. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (66.67) | 29.6817 |
| 2010's | 1 (33.33) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.56) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||