6659-40-1

Basic information

• Product Name: uridine diphosphate 2-deoxyglucose
• Synonyms: uridine diphosphate 2-deoxyglucose
• CAS NO: 6659-40-1
• Molecular Formula: C15H24N2O16P2
• Molecular Weight: 550.3024
• Mol File: 6659-40-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.9g/cm³
• Refractive Index: 1.654
• CAS DataBase Reference: uridine diphosphate 2-deoxyglucose(CAS DataBase Reference)
• NIST Chemistry Reference: uridine diphosphate 2-deoxyglucose(6659-40-1)
• EPA Substance Registry System: uridine diphosphate 2-deoxyglucose(6659-40-1)

Safety Data

• Hazardous Substances Data: 6659-40-1(Hazardous Substances Data)

Usage

General Description

Uridine diphosphate 2-deoxyglucose (UDP-Glc) is a nucleotide sugar involved in various biochemical processes within the body, particularly in the synthesis of glycogen and glycosaminoglycans. It is a key substrate for glycosylation, which is the process of attaching sugar molecules to proteins or lipids, thereby affecting their structure, function, and localization within cells. UDP-Glc is also an essential precursor in the biosynthesis of the polysaccharides found in the cell wall of bacteria, fungi, and plants. Additionally, it plays a crucial role in the regulation of cellular metabolism, energy production, and the immune response. Overall, UDP-Glc is an important molecule with diverse functions in biological systems.

InChI:InChI=1/C15H24N2O16P2/c18-4-7-11(21)12(22)13(23)14(31-7)32-35(27,28)33-34(25,26)29-5-8-6(19)3-10(30-8)17-2-1-9(20)16-15(17)24/h1-2,6-8,10-14,18-19,21-23H,3-5H2,(H,25,26)(H,27,28)(H,16,20,24)/t6-,7+,8+,10+,11+,12-,13+,14+/m0/s1

Upstream product

• 1173-82-6 2'-deoxyuridine-5'-triphosphate 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 
• 42155-08-8 2’-deoxyuridine 5’-monophosphate disodium salt 
• 57-50-1 Sucrose 

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.

Biosynthesis of nucleotide sugars by a promiscuous UDP-sugar pyrophosphorylase from Arabidopsis thaliana (AtUSP)

Nucleotide sugars are activated forms of monosaccharides and key intermediates of carbohydrate metabolism in all organisms. The availability of structurally diverse nucleotide sugars is particularly important for the characterization of glycosyltransferases. Given that limited methods are available for preparation of nucleotide sugars, especially their useful non-natural derivatives, we introduced herein an efficient one-step three-enzyme catalytic system for the synthesis of nucleotide sugars from monosaccharides. In this study, a promiscuous UDP-sugar pyrophosphorylase (USP) from Arabidopsis thaliana (AtUSP) was used with a galactokinase from Streptococcus pneumoniae TIGR4 (SpGalK) and an inorganic pyrophosphatase (PPase) to effectively synthesize four UDP-sugars. AtUSP has better tolerance for C4-derivatives of Gal-1-P compared to UDP-glucose pyrophosphorylase from S. pneumoniae TIGR4 (SpGalU). Besides, the nucleotide substrate specificity and kinetic parameters of AtUSP were systematically studied. AtUSP exhibited considerable activity toward UTP, dUTP and dTTP, the yield of which was 87%, 85% and 84%, respectively. These results provide abundant information for better understanding of the relationship between substrate specificity and structural features of AtUSP.

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