Glucosamine 1-phosphate

Base Information

• Chemical Name: Glucosamine 1-phosphate
• CAS No.: 2152-75-2
• Molecular Formula: C6H14 N O8 P
• Molecular Weight: 259.15
• UNII: BSG3MU7VAE
• DSSTox Substance ID: DTXSID70175855
• Nikkaji Number: J1.531.908I
• Wikidata: Q27094063
• Metabolomics Workbench ID: 51395
• Mol file: 2152-75-2.mol

Synonyms:glucosamine 1-phosphate

Chemical Property of Glucosamine 1-phosphate

Chemical Property:

• Vapor Pressure: 1.09E-16mmHg at 25°C
• Boiling Point: 596°Cat760mmHg
• PKA: 1.73±0.10(Predicted)
• Flash Point: 314.3°C
• PSA: 172.51000
• Density: 1.81g/cm³
• LogP: -2.43770
• Storage Temp.: −20°C
• Solubility.: Water (Sparingly),
• XLogP3: -6.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 259.04570340
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-D-Glucosamine 1-Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OP(=O)(O)O)N)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OP(=O)(O)O)N)O)O)O
• Uses: ALPHA-D-GLUCOSAMINE 1-PHOSPHATE is a phosphorylated glucosamine used in the enzymatic α-glucosaminylation of maltooligosaccharides catalyzed by phosphorylase. A phosphorylated glucosamine used in the enzymatic α-glucosaminylation of maltooligosaccharides catalyzed by phosphorylase.

Technology Process of Glucosamine 1-phosphate

There total 18 articles about Glucosamine 1-phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-azido-2-deozy-α-D-galactopyranosyl 1-dibenzyl phosphate → 2-amino-2-deoxy-α-D-galactopyranosyl 1-phosphate (2152-75-2,19889-76-0,22916-34-3,35946-79-3,26401-96-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 2h; under 2068.59 Torr;

DOI:10.1021/ja982783i

Reference yield: 93.1%

D-galactosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → 2-amino-2-deoxy-α-D-galactopyranosyl 1-phosphate (2152-75-2,19889-76-0,22916-34-3,35946-79-3,26401-96-7)

Guidance literature:

With hydrogenchloride; Bifidobacterium infantis ATCC₁₅₆₉₇ galactokinase; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride; In water; at 37 ℃; for 12h; pH=6.5; Enzymatic reaction;

DOI:10.1039/c5cc03746h

Reference yield: 71.0%

(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-galactopyranosyl) dibenzyl phosphate → 2-amino-2-deoxy-α-D-galactopyranosyl 1-phosphate (2152-75-2,19889-76-0,22916-34-3,35946-79-3,26401-96-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; ethyl acetate; for 60h; under 37503 Torr;

DOI:10.1016/S0008-6215(02)00183-0

upstream raw materials:

D-glucosamine-6-phosphate

O³,O⁴,O⁶-triacetyl-2-amino-O¹-diphenoxyphosphoryl-2-deoxy-α-D-glucopyranose; hydrochloride

3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose

(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucpyranosyl) dibenzyl phosphate

Downstream raw materials:

uridine 5'-(2-amino-2-deoxy-α-D-glucopyranosyl)-diphosphate

uridine 5'-(2-amino-2-deoxy-α-D-galactopyranosyl diphosphate)

3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl dihydrogen phosphate

[13C]-N-acetylglucosamine-1-phosphate

Refernces

• 1、 Alteen, Matthew G.,Busmann, Jil A.,Cardoso, David A.,Davies, Gideon J.,Deen, Matthew C.,Gros, Christina,McCluskey, Adam,Meek, Richard W.,Robinson, Phillip J.,Russell, Cecilia C.,Sangouard, Gontran,Shen, David L.,Tan, Hong-Yee,Vocadlo, David J.. "A Direct Fluorescent Activity Assay for Glycosyltransferases Enables Convenient High-Throughput Screening: Application to O-GlcNAc Transferase". . p. 9601 - 9609. Retrieved 2020/04/09.
• 2、 Li, Lei,Liu, Yonghui,Wang, Wenjun,Cheng, Jiansong,Zhao, Wei,Wang, Peng. "A highly efficient galactokinase from Bifidobacterium infantis with broad substrate specificity". experimental part. p. 35 - 39. Retrieved 2012/08/08.