5572-04-3

Basic information

• Product Name: O^5'-(2-hexopyranosyloxy-1,2-dihydroxy-diphosphoryl)-guanosine
• CAS NO: 5572-04-3
• Molecular Weight: 605.346
• Mol File: 5572-04-3.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: O^5'-(2-hexopyranosyloxy-1,2-dihydroxy-diphosphoryl)-guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: O^5'-(2-hexopyranosyloxy-1,2-dihydroxy-diphosphoryl)-guanosine(5572-04-3)
• EPA Substance Registry System: O^5'-(2-hexopyranosyloxy-1,2-dihydroxy-diphosphoryl)-guanosine(5572-04-3)

Safety Data

• Hazardous Substances Data: 5572-04-3(Hazardous Substances Data)

Upstream product

• 139883-95-7 α-D-mannose 1-phosphate mono-triethylammonium salt 
• 69281-33-0 Guanosine 5'-monophosphate imidazolide 
• 530-26-7 D-Mannose 
• 86-01-1 Guanosine 5'-triphosphate 
• 3458-28-4 D-Mannose 
• 85-32-5 Guanosine 5'-monophosphate 
• 127070-83-1 guanosine 5-monophosphate mono(trioctylammonium) salt 
• 90357-98-5 dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 13242-53-0 acetobromomannose 
• 181427-61-2 C₂₄H₃₃N₅O₂₀P₂ 
• 14356-96-8 5'-guanosine triphosphate, trisodium salt 
• 59-56-3 mannose-1-phosphate 
• 14034-70-9 α-D-mannopyranosyl (bis(cyclohexylammonium)phosphate) 

Downstream Products

• 1093384-49-6 [5''-2H]-GDP-6-deoxy-4-keto-D-mannose 
• 1093384-57-6 [3''-2H]-GDP-6-deoxy-4-keto-D-mannose 
• 154235-70-8 guanosine 5’-diphospho-β-L-fucose 
• 146-91-8 guanosine-5'-diphosphate 
• 1421868-74-7 octyl α-D-mannopyranosyl-(1→4)-α-D-glucopyranosiduronic acid 
• 14843-73-3 2'-O-fucosyllactose 
• 66168-03-4 8-bromoguanosine diphosphate mannose 
• 647036-75-7 GDP-L-gulose 
• 6815-91-4 guanosine 5'-diphospho-β-L-galactopyranoside 
• 18186-48-6 GDP-4-keto-6-deoxy-α-D-mannose 
• 15839-70-0 guanosine-5'-diphospho-β-L-fucose 
• 59571-75-4 methyl 2-O-α-D-mannopyranosyl-α-D-mannopyranoside 
• 50271-62-0 α-D-Manp-(1->2)-α-D-Manp 

Relevant articles and documents

Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose

This paper compares enzymatic and chemical methods for the synthesis of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate from the corresponding nucleoside monophosphates on scales of ~10 g. These nucleoside triphosphates are important as intermediates in Leloir pathway biosyntheses of complex carbohydrates; the nucleoside monophosphates are readily available commercially. The best route to CTP is based on phosphorylation of CMP using adenylate kinase (EC 2.7.4.3); the route to GTP involves phosphorylation of GMP using guanylate kinase (EC 2.7.4.8); chemical deamination of CTP (prepared enzymatically from CMP) is the best synthesis of UTP. For the 10-200-mmol-scale reactions described in this paper, it is more convenient to prepare phosphoenolpyruvate (PEP), used in the enzymatic preparations, from D-(-)-3-phosphoglyceric acid (3-PGA) in the reaction mixture rather than to synthesize PEP in a separate chemical step. The in situ conversion of 3-PGA to PEP requires the coupled action of phosphoglycerate mutase (EC 2.7.5.3) and enolase (EC 4.2.1.11). The enzyme-catalyzed syntheses of uridine 5'-diphosphoglucose (UDP-Glc), uridine 5'-diphosphoglucuronic acid (UDP-GlcUA), and guanosine 5'-diphosphomannose (GDP-Man) illustrate the use of the nucleoside triphosphates.

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.

Efficient enzymatic synthesis of guanosine 5′-diphosphate-sugars and derivatives

An N-acetylhexosamine 1-kinase from Bifidobacterium infantis (NahK-15697), a guanosine 5′-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) were used efficiently for a one-pot three-enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose. This study represents the first facile and efficient enzymatic synthesis of GDP-sugars and derivatives starting from monosaccharides and derivatives.