68733-26-6

Basic information

• Product Name: 2-Azido-2-deoxy-D-galactose
• Synonyms: 2-Azido-2-deoxy-D-galactose;D-Galactose,2-azido-2-deoxy-
• CAS NO: 68733-26-6
• Molecular Formula: C₆H₁₁N₃O₅
• Molecular Weight: 205.16864
• EINECS: 1533716-785-6
• Mol File: 68733-26-6.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Azido-2-deoxy-D-galactose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azido-2-deoxy-D-galactose(68733-26-6)
• EPA Substance Registry System: 2-Azido-2-deoxy-D-galactose(68733-26-6)

Safety Data

• Hazardous Substances Data: 68733-26-6(Hazardous Substances Data)

Usage

General Description

2-Azido-2-deoxy-D-galactose is a chemical compound that belongs to the family of azido sugars, specifically, a derivative of the common sugar galactose. This special sugar has an azido group attached, replacing one of the hydroxyl groups in the sugar molecule. 2-Azido-2-deoxy-D-galactose is an important ingredient in biochemical research due to its unique reaction with other substances. While it retains properties of regular sugars like water solubility, stability, and polar characteristics, the azido group presents the possibility for a click reaction, a type of bioorthogonal chemistry that is quick and specific. Therefore, it is effectively used to mark, track, and manipulate molecules in various biological systems.

Upstream product

• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 90-76-6 D-galactosamine 
• 66-84-2 2-amino-2-deoxy-D-galactose hydrochloride 

Downstream Products

• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 100938-55-4 N-(9H-fluorene-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 100929-00-8 benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 
• 116783-35-8 N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine 
• 99212-30-3 deoxyfuconojirimycin 
• 116265-55-5 N-Benzyl-1,5-didesoxy-1,5-imino-L-fucit 
• 116265-56-6 1,5-Didesoxy-1,5-imino-N-<5-(methoxycarbonyl)pentyl>-L-fucit 
• 116265-49-7 3,4,5-Tri-O-benzoyl-2,6-didesoxy-2,6-imino-D-galactose-trimethylendithioacetal 
• 116265-50-0 2,3,4-Tri-O-benzoyl-1,5-didesoxy-1,5-imino-L-fucit 
• 116265-42-0 2-Azido-6-O-(tert-butyldiphenylsilyl)-2-desoxy-D-galactose-trimethylendithioacetal 
• 116265-44-2 2-Azido-2-desoxy-6-O-trityl-D-galactose-trimethylendithioacetal 
• 116265-54-4 2-Phenyl-(4,5-di-O-benzoyl-2,3-didesoxy-D-galacto-trimethylendithioacetal)-<2,3-d>-2-oxazolin 
• 116265-51-1 2,3,4-Tri-O-benzoyl-1,5-didesoxy-1,5-imino-N-<5-(methoxycarbonyl)pentyl>-L-fucit 
• 116265-46-4 2-Azido-3,4,5-tri-O-benzoyl-2-desoxy-D-galactose-trimethylendithioacetal 

Relevant articles and documents

Synthesis aided structural determination of amyloid-β(1-15) glycopeptides, new biomarkers for Alzheimer's disease

Unique tyrosine glycosylated amyloid-β(1-15) glycopeptides were synthesized with well-defined stereochemistry at the glycosidic linkages. Aided by these glycopeptides and tandem mass spectrometry analysis, the naturally existing amyloid-β glycopeptides, isolated from Alzheimer's disease patients, were determined to contain an α-linked N-acetyl galactosamine at the modified tyrosine 10 residue. Glycosylation can significantly impact the properties of amyloid-β as the glycopeptide has much lower affinity for Cu+ ions.

Enhanced Binding and Reduced Immunogenicity of Glycoconjugates Prepared via Solid-State Photoactivation of Aliphatic Diazirine Carbohydrates

Biological conjugation is an important tool employed for many basic research and clinical applications. While useful, common methods of biological conjugation suffer from a variety of limitations, such as (a) requiring the presence of specific surface-exposed residues, such as lysines or cysteines, (b) reducing protein activity, and/or (c) reducing protein stability and solubility. Use of photoreactive moieties including diazirines, azides, and benzophenones provide an alternative, mild approach to conjugation. Upon irradiation with UV and visible light, these functionalities generate highly reactive carbenes, nitrenes, and radical intermediates. Many of these will couple to proteins in a non-amino-acid-specific manner. The main hurdle for photoactivated biological conjugation is very low yield. In this study, we developed a solid-state method to increase conjugation efficiency of diazirine-containing carbohydrates to proteins. Using this methodology, we produced multivalent carbohydrate-protein conjugates with unaltered protein charge and secondary structure. Compared to carbohydrate conjugates prepared with amide linkages to lysine residues using standard NHS conjugation, the photoreactive prepared conjugates displayed up to 100-fold improved binding to lectins and diminished immunogenicity in mice. These results indicate that photoreactive bioconjugation could be especially useful for in vivo applications, such as lectin targeting, where high binding affinity and low immunogenicity are desired.

Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate

We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl