2140-58-1

Basic information

• Product Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphinic acid
• Synonyms: Diphosphoric acid α-(5'-adenosyl)β-(α-D-glucopyranosyl) ester;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphinic acid;ADP-glucose;ADP-D-GLUCOSE;Adenosine Diphosphate Glucose;Adenosine 5'-diphosphoric acid β-(α-D-glucopyranosyl) ester;ADPG;ADP alpha-D-glucoside
• CAS NO: 2140-58-1
• Molecular Formula: C₁₆H₂₅N₅O₁₅P₂
• Molecular Weight: 589.34
• Mol File: 2140-58-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 997.5°Cat760mmHg
• Flash Point: 557.1°C
• Appearance: /
• Density: 2.42g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.867
• PKA: 1.10±0.50(Predicted)
• CAS DataBase Reference: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphinic acid(2140-58-1)
• EPA Substance Registry System: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-phosphinic acid(2140-58-1)

Safety Data

• Hazardous Substances Data: 2140-58-1(Hazardous Substances Data)

Usage

Definition

ChEBI: An ADP-aldose having alpha-D-glucopyranose as the sugar moiety.

InChI:InChI=1/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)

Upstream product

• 4578-31-8 adenosine-5'-monophosphate disodium salt 
• 57-50-1 Sucrose 
• 99-20-7 TREHALOSE 
• 58-64-0 adenosine 5'-diphosphate 
• 61503-56-8 α-D-glucose-1-phosphate tributylammonium salt 
• 56-65-5 ATP 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 

Downstream Products

• 50-99-7 D-glucose 
• 99-20-7 TREHALOSE 
• 58-64-0 adenosine 5'-diphosphate 

Relevant articles and documents

Exploring the broad nucleotide triphosphate and sugar-1-phosphate specificity of thymidylyltransferase Cps23FL from: Streptococcus pneumonia serotype 23F

Glucose-1-phosphate thymidylyltransferase (Cps23FL) from Streptococcus pneumonia serotype 23F is the initial enzyme that catalyses the thymidylyl transfer reaction in prokaryotic deoxythymidine diphosphate-l-rhamnose (dTDP-Rha) biosynthetic pathway. In this study, the broad substrate specificity of Cps23FL towards six glucose-1-phosphates and nine nucleoside triphosphates as substrates was systematically explored, eventually providing access to nineteen sugar nucleotide analogs.

Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides

As Leloir glycosyltransferases are increasingly being used to prepare oligosaccharides, glycoconjugates, and glycosylated natural products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5′-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium bicarbonate and tributylammonium acetate were the ion-pair reagents of choice for the C18 reversed-phase purification of 6-deoxysugar nucleotides, and hexose or pentose-derived sugar nucleotides, respectively.

Combined enzymatic synthesis of nucleotide (deoxy) sugars from sucrose and nucleoside monophosphates

The synthesis of NDP-glucose 3a-d (N = A, C, U, dU) with sucrose synthase B was combined with the enzymatic synthesis of nucleoside diphosphates 2a-d from their corresponding nucleoside monophosphates 1a-d by different kinases A. Further combination with