2152-75-2

Basic information

• Product Name: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE
• Synonyms: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE;A-D-glucosamine 1-phosphate free acid;α-d-glucosamine 1-phosphate;glucosamine 1-phosphate;alpha-D-glucosamine phosphate;[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate;[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-methylol-tetrahydropyran-2-yl] dihydrogen phosphate;[(2R,3R,4R,5S,6R)-3-azanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
• CAS NO: 2152-75-2
• Molecular Formula: C6H14NO8P
• Molecular Weight: 259.15
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates GBiochemicals and Reagents;Monosaccharide;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 2152-75-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 596°Cat760mmHg
• Flash Point: 314.3°C
• Appearance: /
• Density: 1.81g/cm³
• Vapor Pressure: 1.09E-16mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: −20°C
• Solubility: Water (Sparingly),
• PKA: 1.73±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE(2152-75-2)
• EPA Substance Registry System: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE(2152-75-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2152-75-2(Hazardous Substances Data)

Usage

Description

ALPHA-D-GLUCOSAMINE 1-PHOSPHATE is a phosphorylated derivative of glucosamine, a naturally occurring amino sugar. It plays a crucial role in various biological processes and serves as an essential compound in the synthesis of glycosaminoglycans, which are vital components of extracellular matrix and cell surface molecules.

Uses

Used in Enzymatic Synthesis:
ALPHA-D-GLUCOSAMINE 1-PHOSPHATE is used as a substrate for the enzymatic α-glucosaminylation of maltooligosaccharides. This process is catalyzed by phosphorylase, an enzyme that facilitates the transfer of glucosamine residues to form complex carbohydrate structures.
Used in Pharmaceutical Industry:
ALPHA-D-GLUCOSAMINE 1-PHOSPHATE is utilized in the development of drugs targeting various medical conditions. Its role in the synthesis of glycosaminoglycans makes it a potential candidate for therapeutic applications in treating diseases associated with the dysregulation of these molecules, such as arthritis, cancer, and certain genetic disorders.
Used in Research and Development:
This phosphorylated glucosamine is also employed in research settings to study the mechanisms of glycosaminoglycan synthesis and its implications in cellular processes. Understanding the role of ALPHA-D-GLUCOSAMINE 1-PHOSPHATE in these pathways can lead to the discovery of novel therapeutic strategies and the development of new drugs for various diseases.

InChI:InChI=1/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6-/m1/s1

Upstream product

• 79781-69-4 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 79184-08-0 3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose 
• 35946-68-0 O³,O⁴,O⁶-triacetyl-2-amino-O¹-diphenoxyphosphoryl-2-deoxy-α-D-glucopyranose; hydrochloride 
• 6665-06-1 D-glucosamine-6-phosphate 
• 90-76-6 D-galactosamine 
• 1334525-86-8 2-azido-2-deoxy-D-glucopyranose-1-(dihydrogen phosphate) 
• 1355005-35-4 2-azido-2-deoxy-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 884856-12-6 (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl phosphate 

Downstream Products

• 17479-06-0 uridine 5'-(2-amino-2-deoxy-α-D-galactopyranosyl diphosphate) 
• 1109-79-1 uridine 5'-(2-amino-2-deoxy-α-D-glucopyranosyl)-diphosphate 
• 16503-17-6 [13C]-N-acetylglucosamine-1-phosphate 
• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 92283-18-6 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl dihydrogen phosphate 
• 28446-21-1 N-acetylglucosamine-1-phosphate 

Relevant articles and documents

Allosteric Modulation of the Faecalibacterium prausnitzii Hepatitis Delta Virus-like Ribozyme by Glucosamine 6-Phosphate: The Substrate of the Adjacent Gene Product

Self-cleaving ribozymes were discovered 30 years ago and have been found throughout nature, from bacteria to animals, but little is known about their biological functions and regulation, particularly how cofactors and metabolites alter their activity. A hepatitis delta virus-like self-cleaving ribozyme maps upstream of a phosphoglucosamine mutase (glmM) open reading frame in the genome of the human gut bacterium Faecalibacterium prausnitzii. The presence of a ribozyme in the untranslated region of glmM suggests a regulation mechanism of gene expression. In the bacterial hexosamine biosynthesis pathway, the enzyme glmM catalyzes the isomerization of glucosamine 6-phosphate into glucosamine 1-phosphate. In this study, we investigated the effect of these metabolites on the co-transcriptional self-cleavage rate of the ribozyme. Our results suggest that glucosamine 6-phosphate, but not glucosamine 1-phosphate, is an allosteric ligand that increases the self-cleavage rate of drz-Fpra-1, providing the first known example of allosteric modulation of a self-cleaving ribozyme by the substrate of the adjacent gene product. Given that the ribozyme is activated by the glmM substrate, but not the product, this allosteric modulation may represent a potential feed-forward mechanism of gene expression regulation in bacteria.

Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Galacto-N-biose (GNB) derivatives were efficiently synthesized from galactose derivatives via a one-pot two-enzyme system containing two promiscuous enzymes from Bifidobacterium infantis: a galactokinase (BiGalK) and a d-galactosyl-β1-3-N-acetyl-d-hexosamine phosphorylase (BiGalHexNAcP). Mono-sialyl and di-sialyl galacto-N-biose derivatives were then prepared using a one-pot two-enzyme system containing a CMP-sialic acid synthetase and an α2-3-sialyltransferase or an α2-6-sialyltransferase.

Artificial N-functionalized UDP-glucosamine analogues as modified substrates for N-acetylglucosaminyl transferases

Analogues of UDP-GlcNAc modified at the 2-acetamido group of the GlcNAc moiety were prepared in order to study their role in the mechanism of N-acetylglucosaminyl transferase mediated glycosylation reactions. The structural analogues with N-formyl-, N-pro