72-87-7

Basic information

• Product Name: 2-Deoxy-2-(acetylamino)-D-glucopyranose
• Synonyms: 2-Deoxy-2-(acetylamino)-D-glucopyranose;N-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide
• CAS NO: 72-87-7
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21
• Product Categories: Non-natural amino acids
• Mol File: 72-87-7.mol

Chemical Properties

• Boiling Point: 595.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• PKA: 12.04±0.70(Predicted)
• CAS DataBase Reference: 2-Deoxy-2-(acetylamino)-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Deoxy-2-(acetylamino)-D-glucopyranose(72-87-7)
• EPA Substance Registry System: 2-Deoxy-2-(acetylamino)-D-glucopyranose(72-87-7)

Safety Data

• Hazardous Substances Data: 72-87-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
2-Deoxy-2-(acetylamino)-D-glucopyranose is used as a therapeutic agent for promoting joint health, as it has been studied for its potential to alleviate symptoms associated with osteoarthritis and other joint conditions. Its role in maintaining healthy cartilage and reducing inflammation contributes to its effectiveness in this application.
Used in Skincare Applications:
In the cosmetics industry, 2-Deoxy-2-(acetylamino)-D-glucopyranose is used as an active ingredient in skincare products for treating skin conditions such as eczema and acne. Its potential anti-inflammatory and immune-modulating effects make it a valuable component in formulations aimed at improving skin health and reducing inflammation.
Used in Nutritional Supplements:
2-Deoxy-2-(acetylamino)-D-glucopyranose is used as a dietary supplement to support overall health and well-being. Its potential health benefits, including joint health promotion and immune modulation, make it a popular choice for consumers seeking natural ways to enhance their health.
Used in Research Applications:
In the scientific community, 2-Deoxy-2-(acetylamino)-D-glucopyranose is used as a research tool to study its potential health benefits and mechanisms of action. Its presence in the exoskeleton of insects, fungi, and bacterial cell walls makes it an important compound for understanding the structure and function of chitin and its role in various biological processes.

Upstream product

• 19342-33-7 N-acetyl neuraminic acid 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 67-56-1 methanol 
• 42890-21-1 2-acetamido-2-deoxy-D-mannose diethyl dithioacetal 
• 7732-18-5 water 
• 2776-93-4 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 128459-09-6 N-acetyl-N-methoxyacetamide 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-24-7 acetic anhydride 
• 2776-93-4 2-acetamido-1-N-(L-aspart-4-oyl)-2-deoxy-β-D-glucopyranosylamine 
• 120489-33-0 methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside 
• 97055-07-7 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine 

Downstream Products

• 98-01-1 furfural 
• 141-46-8 Glycolaldehyde 
• 28876-37-1 2-acetamido-2-deoxy-D-mannono-1,4-lactone 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 161060-29-3 2-acetamido-2-deoxy-5,6-O-benzylidene-D-mannono-1,4-lactone 
• 161060-30-6 2-acetamido-5,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-D-mannono-1,4-lactone 
• 155544-70-0 2-acetamido-6-O-acetyl-2,3-didehydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone 
• 14635-94-0 2-amino-2-deoxy-D-mannitol 
• 58718-38-0 (2S,4S,5R,6R)-5-Acetylamino-6-[(R)-1,2-dihydroxy-3-(2-hydroxy-propionyloxy)-propyl]-2,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 209977-51-5 β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-mannopyranose 
• 209977-51-5 β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-mannopyranose 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 58546-02-4 2-acetamido-2,3-dideoxy-α-D-erythro-hex-2-enofuranose 
• 1262206-14-3 2-acetamido-3,6-anhydro-2-deoxy-β-D-mannofuranose 

Relevant articles and documents

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives

Abstract: A new series of glycosyl benzofuranylthiazole derivatives were designed, synthesized, characterized, and evaluated as potential candidates to treat Alzheimer’s disease. The compounds have been synthesized by the cyclocondensation of glycosyl thiourea with a variety of 2-(bromoacetyl)benzofurans. The reaction conditions have been optimized, and good yields (79–95%) have been obtained. The synthesized compounds showed different degrees of cholinesterase inhibitory activity.

Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.

Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation

Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.

Biochemical Characterization and Structural Analysis of a β- N-Acetylglucosaminidase from Paenibacillus barengoltzii for Efficient Production of N-Acetyl- d -glucosamine

Bioproduction of N-acetyl-d-glucosamine (GlcNAc) from chitin, the second most abundant natural renewable polymer on earth, is of great value in which chitinolytic enzymes play key roles. In this study, a novel glycoside hydrolase family-18 β-N-acetylglucosaminidase (PbNag39) from Paenibacillus barengoltzii suitable for GlcNAc production was identified and biochemically characterized. It possessed a unique shallow catalytic groove (5.8 ?) as well as a smaller C-terminal domain (solvent-accessible surface area, 5.1 × 103 ?2) and exhibited strict substrate specificity toward N-acetyl chitooligosaccharides (COS) with GlcNAc as the sole product, showing a typical manner of action of β-N-acetylglucosaminidases. Thus, an environmentally friendly bioprocess for GlcNAc production from ball-milled powdery chitin by an enzyme cocktail reaction was further developed. By using the new route, the powdery chitin conversion rate increased from 23.3% (v/v) to 75.3% with a final GlcNAc content of 22.6 mg mL-1. The efficient and environmentally friendly bioprocess may have great application potential in GlcNAc production.

Enzymatic synthesis of trideuterated sialosides

Sialic acids are a family of acidic monosaccharides often found on the termini of cell surface proteins or lipid glycoconjugates of higher animals. Herein we describe the enzymatic synthesis of the two isotopically labeled sialic acid derivatives d3-X-Gal-a-2,3-Neu5Ac and d3-X-Gal-a-2,3-Neu5Gc. Using deuterium oxide as the reaction solvent, deuterium atoms could be successfully introduced during the enzymatic epimerization and aldol addition reactions when the sialosides were generated. NMR and mass spectrometric analyses confirmed that the resulting sialosides were indeed tri-deuterated. These compounds may be of interest as internal standards in liquid chromatography/mass spectrometric assays for biochemical or clinical studies of sialic acids. This was further exemplified by the use of this tri-deuterated sialosides as internal standards for the quantification of sialic acids in meat and egg samples.

Aromatic butenolides produced by a soil ascomycete Auxarthron sp. KCB15F070 derived from a volcanic island

LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.

Structures of triterpenoids from the leaves of Lansium domesticum

From the methanolic extract of the leaves of Lansium domesticum, three new onoceranoid-type triterpenoids, lansium acids X–XII and a new cycloartane-type triterpene, lansium acid XIII, were isolated. The chemical structures of the isolated new compounds were elucidated on the basis of chemical/physicochemical evidence. For new onoceranoid-type triterpenoids, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. The isolated onoceranoid-type triterpenoids showed antimutagenic effects in the Ames assay against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1).

Structures and Antimutagenic Effects of Onoceranoid-Type Triterpenoids from the Leaves of Lansium domesticum

A methanol extract of the dried leaves of Lansium domesticum showed antimutagenic effects against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) and 2-amino-1-methyl-6-phenylimidazo[4,5-bI]pyridine (PhIP) using the Ames assay. Nine new onoceranoid-type triterpenoids, lansium acids I-IX (1-9), and nine known compounds (10-16) were isolated from the extract. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. The absolute stereostructures of the new compounds were determined via their electronic circular dichroism spectra. Several isolated onoceranoid-type triterpeneoids showed antimutagenic effects in an in vitro Ames assay. Moreover, oral intake of a major constituent, lansionic acid (10), showed antimutagenic effects against PhIP in an in vivo micronucleus test.