108321-48-8

Basic information

• Product Name: 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE
• Synonyms: 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-B-D-MANNOPYRANOSE;1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE;1-2-3-4-tetra-O-acetyl-6*diphenylphosphoryl-B-D-M;1-2-3-4-TETRA-O-ACETYL-6*DIPHENYLPHOSPHO RYL-B-D-MAN;1,2,3,4-tetra-o-acetyl-6-diphenylphosphoryl-β-d-mannopyranose;1,2,3,4-Τetraacetate 6-(Diphenyl phosphate) β-D-Mannopyranose;beta-D-Mannopyranose 1,2,3,4-tetraacetate 6-(diphenyl phosphate)
• CAS NO: 108321-48-8
• Molecular Formula: C₂₆H₂₉O₁₃P
• Molecular Weight: 580.47
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Monosaccharide;Phosphorylating and Phosphitylating Agents
• Mol File: 108321-48-8.mol

Chemical Properties

• Melting Point: 113-115°C
• Appearance: /
• Refractive Index: 1.552
• Storage Temp.: −20°C
• CAS DataBase Reference: 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE(108321-48-8)
• EPA Substance Registry System: 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE(108321-48-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 108321-48-8(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry and Molecular Biology:
1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE is used as a synthetic intermediate for the preparation of D-Mannose 6-phosphate residues. These residues serve as subcellular sorting signals in the lysosomal targeting of acid hydrolases, which are essential enzymes involved in the degradation of biomolecules within lysosomes.
Used in Pharmaceutical Industry:
1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE is used as a key building block in the synthesis of therapeutic agents targeting lysosomal storage disorders. These disorders are caused by the deficiency or malfunction of lysosomal enzymes, leading to the accumulation of undigested materials in lysosomes. 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE can be utilized to develop drugs that enhance the delivery and functionality of these enzymes, thereby alleviating the symptoms of the disease.
Used in Chemical Research:
1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE is used as a research tool in the study of carbohydrate chemistry, enzymatic reactions, and glycobiology. Its unique structure allows scientists to investigate the role of sugar moieties in various biological processes and develop new strategies for modulating these processes.
Used in Material Science:
1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE can be employed in the development of advanced materials with specific properties, such as stimuli-responsive hydrogels, drug delivery systems, and biosensors. 1,2,3,4-TETRA-O-ACETYL-6-DIPHENYLPHOSPHORYL-BETA-D-MANNOPYRANOSE's ability to interact with other molecules and its solid-state properties make it a promising candidate for these applications.

InChI:InChI=1/C26H29O13P/c1-16(27)33-23-22(37-26(36-19(4)30)25(35-18(3)29)24(23)34-17(2)28)15-32-40(31,38-20-11-7-5-8-12-20)39-21-13-9-6-10-14-21/h5-14,22-26H,15H2,1-4H3/t22?,23-,24+,25-,26-/m1/s1

Upstream product

• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 28154-37-2 1,2,3,4-tetra-O-acetyl-β-D-mannopyranose 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 108266-23-5 2,3,4-tri-O-acetyl-6-O-<(diphenoxy)phosphoryl>-α-D-mannopyranosyl bromide 
• 19504-70-2 D-mannose 1α,6-bisphosphate 
• 102112-80-1 O²,O³,O⁴-triacetyl-O⁶-diphenoxyphosphoryl-α-D-glucopyranosyl bromide 
• 10139-18-1 6-phospho-α-D-glucopyranosyl-1-phosphate 

Relevant articles and documents

Kinetic analysis of β-phosphoglucomutase and its inhibition by magnesium fluoride

The isomerization of β-glucose-1 -phosphate (βG1 P) to β-glucose-6-phosphate (G6P) catalyzed by β-phosphoglucomutase (βPGM) has been examined using steady- and presteady-state kinetic analysis. In the presence of low concentrations of β-glucose-1,6- bisphosphate (βG16BP), the reaction proceeds through a Ping Pong Bi Bi mechanism with substrate inhibition (K cat = 65 s -1 , K βG1P = 15 μM, K βG1P = 0.7 μM, K i = 122 μM). If αG16BP is used as a cofactor, more complex kinetic behavior is observed, but the nonlinear progress curves canbe fit to reveal further catalytic parameters (k cat = 74 s-1 , K βG1P = 15 μM, K βG16BP = 0.8 μM, K i = 122 μM, K αG16BP = 91μM for productive binding, K αG16BP = 21 μM for unproductive binding). These data reveal that variations in the substrate structure affect transition-state affinity (approximately 140 000-fold in terms of rate acceleration) substantially more than ground-state binding (110-fold in terms of binding affinity). When fluoride and magnesium ions are present, time-dependent inhibition of the βPGM is observed. The concentration dependence of the parameters obtained from fitting these progress curves shows that a βG1 P-MgF 3- βPGM inhibitory complex is formed under the reaction conditions. The overall stability constant for this complex is approximately 2 × 10 -16 M 5 and suggests an affinity of the MgF 3 - moiety to this transition-state analogue (TSA) of ≤70 nM. The detailed kinetic analysis shows how a special type of TSA that does not exist in solution is assembled in the active site of an enzyme. Further experiments show that under the conditions of previous structural studies, phosphorylated glucose only persists when bound to the enzyme as the TSA. The preference for TSA formation when fluoride is present, and the hydrolysisof substrates when it is not, rules out the formation of a stable penta valent phosphorane intermediate in the active site of βPGM.