16503-17-6

Basic information

• Product Name: 2-(acetylamino)-2-deoxy-1-O-phosphono-D-glucopyranose
• Synonyms: 901851-43-2
• CAS NO: 16503-17-6
• Molecular Formula: C₈H₁₆NO₉P
• Molecular Weight: 301.1877
• Mol File: 16503-17-6.mol
• Article Data: 11

Chemical Properties

• Density: 1.7g/cm³
• Refractive Index: 1.579
• CAS DataBase Reference: 2-(acetylamino)-2-deoxy-1-O-phosphono-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(acetylamino)-2-deoxy-1-O-phosphono-D-glucopyranose(16503-17-6)
• EPA Substance Registry System: 2-(acetylamino)-2-deoxy-1-O-phosphono-D-glucopyranose(16503-17-6)

Safety Data

• Hazardous Substances Data: 16503-17-6(Hazardous Substances Data)

Upstream product

• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 
• 72-87-7 N-acetyl-D-galactosamine 
• 19889-76-0 D-glucosamine 1-phosphate 
• 72-89-9 acetylcoenzyme A 
• 72-87-7 N-acetyl-D-galactosamine 
• 56-65-5 ATP 
• 2152-75-2 2-amino-2-deoxy-α-D-galactopyranosyl 1-phosphate 
• 72-89-9 S-acetyl coenzyme A 
• 389-48-0 2-Acetamido-2-deoxy-α-D-glucopyranosyl fluoride 
• 439-02-1 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 14200-67-0 N,N'-diacetylchitobiose 
• 10036-64-3 N-acetyl-D-glucosamine 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 16426-39-4 UDP-α-D-N-acetylglucosamine 
• 16426-39-4 uridine diphosphate N-acetylglucosamine 
• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 

Relevant articles and documents

Two-step enzymatic synthesis of UDP-N-acetylgalactosamine

UDP-GalNAc has been synthesised with high yield from GalNAc, UTP and ATP using recombinant human GalNAc kinase GK2 and UDP-GalNAc pyrophosphorylase AGX1. Both enzymes have been prepared in one step from 1 L cultures of transformed Escherichia coli and the UDP-GalNAc produced has been purified by a simple procedure. The method described is a rapid and efficient means to produce UDP-GalNAc as well as analogues like UDP-N-azidoacetylgalactosamine (UDP-GalNAz).

ACTIVATED N-ACETYLATED SUGARS AND OLIGOSACCHARIDES

The invention relates to production of uridine-5'diphospho-N-acetylglucosamine and uridine-5'diphospho-N-acetylgalactosamine. The invention further relates to the production of lacto-/V-triose II and globotetraose.

Biosynthesis of the carbamoylated D-gulosamine moiety of streptothricins: Involvement of a guanidino-N-glycosyltransferase and an N-acetyl-D-gulosamine deacetylase

Streptothricins (STNs) are atypical aminoglycosides containing a rare carbamoylated D-gulosamine (D-GulN) moiety, and the antimicrobial activity of STNs has been exploited for crop protection. Herein, the biosynthetic pathway of the carbamoylated D-GulN moiety was delineated. An N-acetyl-D-galactosamine is first attached to the streptolidine lactam by the glycosyltransferse StnG and then epimerized to N-acetyl-D-gulosamine by the putative epimerase StnJ. After carbamoylation by the carbamoyltransferase StnQ, N-acetyl-D-GulN is deacetylated by StnI to furnish the carbamoylated D-GulN moiety. In vitro studies characterized two novel enzymes: StnG is an unprecedented GT-A fold N-glycosyltransferase that glycosylates the imine nitrogen atom of guanidine, and StnI is the first reported N-acetyl-D-GulN deacetylase. The dynamic duo: Two novel enzymes, StnG and StnI, have been found to be involved in the biosynthetic pathway of the carbamoylated D-gulosamine moiety in streptothricins. StnG is a GT-A fold glycosyltransferase that catalyzes the unprecedented attachment of a sugar to the imine nitrogen atom of a guanidine group; StnI catalyzes the deacetylation of the N-acetyl-D-gulosamine moiety.

Substrate specificity of galactokinase from Streptococcus pneumoniae TIGR4 towards galactose, glucose, and their derivatives

Galactokinases (GalKs) have attracted significant research attention for their potential applications in the enzymatic synthesis of unique sugar phosphates. The galactokinase (GalKSpe4) cloned from Streptococcus pneumoniae TIGR4 presents a remarkably broad substrate range including 14 diverse natural and unnatural sugars. TLC and MS studies revealed that GalKSpe4 had relaxed activity towards galactose derivatives with modifications on the C-6, 4- or 2-positions. Additionally, GalKSpe4 can also tolerate glucose while glucose derivatives with modifications on the C-6, 4- or 2-positions were unacceptable. More interestingly, GalKSpe4 can phosphorylate l-mannose in moderate yield (43%), while other l-sugars such as l-Gal cannot be recognized by this enzyme. These results are very significant because there is rarely enzyme reported that can phosphorylate such uncommon substrates as l-mannose.