59-56-3

Basic information

• Product Name: glucose 1-(dihydrogen phosphate)
• Synonyms: glucose 1-(dihydrogen phosphate);Glucose-1-phosphate;[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid;Glucose monophosphate.;α-D-[1-13C]Glucopyranosyl 1-phosphate;alpha-D-glucose-1-P;alpha-glucose-1-phosphate;D-glucose-alpha-1-phosphate
• CAS NO: 59-56-3
• Molecular Formula: C₆H₁₃O₉P
• Molecular Weight: 276.135181
• EINECS: 200-435-8
• Product Categories: 13C & 2H Sugars
• Mol File: 59-56-3.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 602.991 °C at 760 mmHg
• Flash Point: 318.478 °C
• Appearance: /
• Density: 1.906 g/cm³
• Refractive Index: 1.606
• PKA: pKa: 6.504(25°C)
• CAS DataBase Reference: glucose 1-(dihydrogen phosphate)(CAS DataBase Reference)
• NIST Chemistry Reference: glucose 1-(dihydrogen phosphate)(59-56-3)
• EPA Substance Registry System: glucose 1-(dihydrogen phosphate)(59-56-3)

Safety Data

• RIDADR: 1759
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 59-56-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A D-glucopyranose 1-phosphate in which the anomeric centre has alpha-configuration.

Purification Methods

Two litres of a 5% aqueous solution of the phosphate are purified by adjusting the pH to 3.5 with glacial acetic acid (+ 3g of charcoal) and filtering. An equal volume of EtOH is added, the pH is adjusted to 8.0 (glass electrode) and the solution is stored at 3o overnight. The precipitate is filtered off, dissolved in 1.2L of distilled water, filtered and an equal volume of EtOH is added. After standing at 0o overnight, the crystals are collected at the centrifuge and washed with 95% EtOH, then absolute EtOH, ethanol/diethyl ether (1:1), and diethyl ether. [Sutherland & Wosilait, J Biol Chem 218 459 1956.] Its barium salt can be crystallised from water and EtOH. Heavy metal impurities are removed by passage of an aqueous solution (ca 1%) through an Amberlite IR-120 column (in the appropriate H+, Na+ or K+ forms). Di-K salt crystallises as a dihydrate from EtOH. [see McGready Biochemical Preparations 4 63 1955.] [Beilstein 17/8 V 247.]

InChI:InChI=1/C6H13O9P/c7-1-2-3(8)4(9)5(6(10)14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6+/m1/s1

Upstream product

• 4768-77-8 exo-3,4,6-tri-O-acetyl-1,2-O-(tert-butyl orthoacetyl)-α-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 3256-04-0 laminaritriose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 723729-16-6 D-mannopyranose 6-phosphate 
• 90357-98-5 dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 25546-57-0 dibenzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate 
• 10139-18-1 glucosee 1,6-diphosphate 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 99-20-7 TREHALOSE 
• 81347-80-0 adenosin 5'-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl diphosphate) 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 1144104-32-4 (2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl) dibenzyl phosphate 

Downstream Products

• 154235-70-8 guanosine 5’-diphospho-β-L-fucose 
• 991-43-5 guanosine 5'-diphospho-D-mannose 
• 133-89-1 UDP-glucose 
• 133-89-1 Uridine diphosphate mannose 
• 50787-09-2 β-Galp-(1->3)-GlcNAc 
• 6659-40-1 dUDP-Glc 
• 69557-93-3 O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose 
• 5077-26-9 3-O-β-D-glucopyranosyl-D-xylose 
• 7115-19-7 methyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside 
• 14000-31-8 pyrophosphoric acid 
• 10596-32-4 [difluoro(phosphono)methyl]phosphonic acid 
• 10595-93-4 1-(fluoromethylene)-1,1-bisphosphonic acid 
• 1984-15-2 Methylenediphosphonic acid 
• 26212-72-6 laminaritetraose 

Relevant articles and documents

Kinetic and NMR spectroscopic study of the chemical stability and reaction pathways of sugar nucleotides

The alkaline cleavage of two types of sugar nucleotides has been studied by 1H and 31P NMR in order to obtain information on the stability and decomposition pathways in aqueous solutions under alkaline conditions. The reaction of glucose 1-UDP is straightforward, and products are easy to identify. The results obtained with ribose 5-UDP and ribose 5-phosphate reveal, in contrast, a more complex reaction system than expected, and the identification of individual intermediate species was not possible. Even though definite proof for the mechanisms previously proposed could not be obtained, all the spectroscopic evidence is consistent with them. Results also emphasise the significant effect of conditions, pH, ionic strength, and temperature, on the reactivity under chemical conditions.

Chemical and enzymatic synthesis of the alginate sugar nucleotide building block: GDP-D-mannuronic acid

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A mutant of phosphomannomutase1 retains full enzymatic activity, but is not activated by IMP: Possible implications for the disease PMM2-CDG

The most frequent disorder of glycosylation, PMM2-CDG, is caused by a deficiency of phosphomannomutase activity. In humans two paralogous enzymes exist, both of them require mannose 1,6-bis-phosphate or glucose 1,6-bis-phosphate as activators, but only phospho-mannomutase1 hydrolyzes bis-phosphate hexoses. Mutations in the gene encoding phos-phomannomutase2 are responsible for PMM2-CDG. Although not directly causative of the disease, the role of the paralogous enzyme in the disease should be clarified. Phosphoman-nomutase1 could have a beneficial effect, contributing to mannose 6-phosphate isomerization, or a detrimental effect, hydrolyzing the bis-phosphate hexose activator. A pivotal role in regulating mannose-1phosphate production and ultimately protein glycosylation might be played by inosine monophosphate that enhances the phosphatase activity of phosphoman-nomutase1. In this paper we analyzed human phosphomannomutases by conventional enzymatic assays as well as by novel techniques such as 31P-NMR and thermal shift assay. We characterized a triple mutant of phospomannomutase1 that retains mutase and phosphatase activity, but is unable to bind inosine monophosphate.