2-acetamido-2-deoxy-D-mannose

Base Information

• Chemical Name: 2-acetamido-2-deoxy-D-mannose
• CAS No.: 3615-17-6
• Molecular Formula: C8H15NO6
• Molecular Weight: 221.21
• UNII: X80PR7P73R
• DSSTox Substance ID: DTXSID90963918
• Nikkaji Number: J149.444I
• Wikidata: Q27293654
• Mol file: 3615-17-6.mol

Synonyms:Mannose,2-acetamido-2-deoxy-, D- (8CI);N-Acetyl-b-D-mannosamine;N-Acetylmannosamine;

Chemical Property of 2-acetamido-2-deoxy-D-mannose

Chemical Property:

• Vapor Pressure: 1.18E-16mmHg at 25°C
• Melting Point: 205 °C
• Refractive Index: 1.575
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 13.04±0.20(Predicted)
• Flash Point: 313.9 °C
• PSA: 119.25000
• Density: 1.5 g/cm³
• LogP: -2.68670
• Storage Temp.: -20°C Freezer
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 221.08993720
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

98%, ^*data from raw suppliers

N-Acetyl-D-mannosamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(C=O)C(C(C(CO)O)O)O
• Isomeric SMILES: CC(=O)N[C@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
• Uses: A derivative of D-Mannosamine (M167000).

Technology Process of 2-acetamido-2-deoxy-D-mannose

There total 16 articles about 2-acetamido-2-deoxy-D-mannose 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: 90.0%

N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → N-acetyl-D-mannosamine (3615-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; aldolase;

DOI:10.1021/ja982950e

Reference yield:

acetyl Coenzyme A + D-galactosamine (1948-54-5,2494-50-0,2636-92-2,3416-24-8,6915-39-5,7535-00-4,14307-02-9,14307-08-5,14307-09-6,14307-12-1,14307-14-3,14635-95-1,26315-48-0,27799-64-0,27799-65-1,69839-78-7,72904-60-0) → N-acetylgalactosamine (134-61-2,3615-17-6,4773-29-9,6813-82-7,7436-28-4,7512-17-6,20770-61-0,20880-43-7,20880-45-9,23583-38-2,23655-50-7,31022-50-1,50985-77-8,134451-94-8,149054-75-1,1811-31-0,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With human recombinant N-acetyltransferase; In aq. buffer; at 37 ℃; for 2h; pH=8; Enzymatic reaction;

DOI:10.1016/j.carres.2018.11.011

Reference yield:

2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) → N-acetylgalactosamine (134-61-2,3615-17-6,4773-29-9,6813-82-7,7436-28-4,7512-17-6,20770-61-0,20880-43-7,20880-45-9,23583-38-2,23655-50-7,31022-50-1,50985-77-8,134451-94-8,149054-75-1,1811-31-0,282727-46-2,478518-83-1,127959-06-2,78393-48-3)

Guidance literature:

With UDP-glucose 4-epimerase; N-acetylhexosamine 1-kinase; UDP-glucose-galactose 1-phosphate uridylyl transferase; ATP; magnesium chloride; at 30 ℃; for 120h; pH=6.5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.carres.2011.08.032

upstream raw materials:

acetic anhydride

pyridine

2-acetamido-2-deoxy-D-glucose

nickel diacetate

Refernces

• 1、 Timms, Nicole,Windle, Claire L.,Polyakova, Anna,Ault, James R.,Trinh, Chi H.,Pearson, Arwen R.,Nelson, Adam,Berry, Alan. "Structural Insights into the Recovery of Aldolase Activity in N-Acetylneuraminic Acid Lyase by Replacement of the Catalytically Active Lysine with γ-Thialysine by Using a Chemical Mutagenesis Strategy". . p. 474 - 481. Retrieved 2013/05/08.
• 2、 Inoue, Kousuke,Nishimoto, Mamoru,Kitaoka, Motomitsu. "One-pot enzymatic production of 2-acetamido-2-deoxy-D-galactose (GalNAc) from 2-acetamido-2-deoxy-D-glucose (GlcNAc)". experimental part. p. 2432 - 2436. Retrieved 2011/12/15.