20379-59-3

Usage

Uses

Used in Biochemical and Glycosylation Studies:
1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a precursor in the synthesis of glycoconjugates for the study of carbohydrate structures and their biological functions. Its unique azide group allows for selective bioorthogonal labeling and functionalization of glycoconjugates in biological systems, making it a valuable tool in chemical biology and glycobiology research.
Used in Enzyme Research:
1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is used as a substrate for enzymes such as glycosidases and glycosyltransferases, enabling the investigation of enzyme mechanisms, specificity, and activity in glycosylation reactions.
Used in Carbohydrate-Protein Interaction Studies:
1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is utilized in the development of glycoarrays, which are high-throughput tools for studying carbohydrate-protein interactions. These arrays provide insights into the binding specificities and affinities of proteins for different carbohydrate structures, aiding in the understanding of molecular recognition processes in biological systems.
Used in Drug Discovery and Vaccine Development:
1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE is employed in the preparation of glycoprotein mimics, which are used to investigate the role of glycosylation in protein function and stability. These mimics are valuable for the development of new drugs and vaccines targeting glycosylated proteins or pathogens.

InChI:InChI=1/C6H11N3O5/c7-9-8-5(3(12)1-10)6(14)4(13)2-11/h2-6,10,12-14H,1H2/t3-,4+,5-,6-/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 20379-61-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 
• 25775-97-7 2,4-dinitrophenyl β-D-glucopyranoside 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 85917-84-6 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl azide 
• 100639-11-0 N-(β-D-glucopyranosyl)triphenylphosphine imide 
• 160712-36-7 (2R,3R,4S,5S,6R)-2-Azido-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 6983-36-4 N-acetyl-β-D-glucopyranosylamine 
• 73174-37-5 4,6-O-benzylidene-β-D-glucopyranosyl azide 
• 3757-90-2 2-acetamido-2-deoxy-6-O-β-D-glucopyranosyl-D-glucopyranoside 
• 1046453-81-9 Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester 
• 1046453-80-8 Nα-(benzyloxycarbonyl)-Nγ-(β-D-glucopyranosyl)-L-asparagine O-methyl ester 
• 1037821-58-1 N-acetyl-L-phenylalanine (1'-(β-D-glucopyranosyl)-1'H-[1',2',3']-triazol-4-yl)methylamide 
• 1037821-53-6 4-(1'-hydroxycyclohexyl)-1-(β-D-glucopyranosyl)-1H-[1,2,3]-triazole 
• 26295-49-8 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-phenyltriazol-1-yl)tetrahydropyran-3,4,5-triol 
• 1202249-81-7 N-(N-benzyloxycarbonyl-β-alanyl)-β-D-glucopyranosylamine 
• 13245-34-6 N-(N-(benzyloxycarbonyl)glycyl)-β-D-glucopyranosylamine 

Relevant academic research and scientific papers

Switching between X-Pyrano-, X-Furano-, and Anhydro- X-pyranoside Synthesis (X = C, N) under Lewis acid Catalyzed Conditions

A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)3) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides), or are virtually unknown (anhydro-C-pyranosides), which mechanistically arise from whether a direct substitution, isomerization/substitution, or substitution/isomerization occurs, respectively.

Identification of the acid/base catalyst of a glycoside hydrolase family 3 (GH3) β-glucosidase from Aspergillus niger ASKU28

Background The commercially important glycoside hydrolase family 3 (GH3) β-glucosidases from Aspergillus niger are anomeric-configuration-retaining enzymes that operate through the canonical double-displacement glycosidase mechanism. Whereas the catalytic nucleophile is readily identified across all GH3 members by sequence alignments, the acid/base catalyst in this family is phylogenetically variable and less readily divined. Methods In this report, we employed three-dimensional structure homology modeling and detailed kinetic analysis of site-directed mutants to identify the catalytic acid/base of a GH3 β-glucosidase from A. niger ASKU28. Results In comparison to the wild-type enzyme and other mutants, the E490A variant exhibited greatly reduced k cat and kcat/Km values toward the natural substrate cellobiose (67,000- and 61,000-fold, respectively). Correspondingly smaller kinetic effects were observed for artificial chromogenic substrates p-nitrophenyl β-d-glucoside and 2,4-dinitrophenyl β-d-glucoside, the aglycone leaving groups of which are less dependent on acid catalysis, although changes in the rate-determining catalytic step were revealed for both. pH-rate profile analyses also implicated E490 as the general acid/base catalyst. Addition of azide as an exogenous nucleophile partially rescued the activity of the E490A variant with the aryl β-glucosides and yielded β-glucosyl azide as a product. Conclusions and general significance These results strongly support the assignment of E490 as the acid/base catalyst in a β-glucosidase from A. niger ASKU28, and provide crucial experimental support for the bioinformatic identification of the homologous residue in a range of related GH3 subfamily members.

Direct azidation of unprotected carbohydrates under Mitsunobu conditions using hydrazoic acid

A single step procedure for the direct and regioselective synthesis of carbohydrate azides from unprotected sugars using hydrazoic acid under Mitsunobu conditions is reported. A series of mono-, di-, or triazido polyhydroxylated systems are described.