Keto-Deoxy-Nonulonic acid

Base Information

• Chemical Name: Keto-Deoxy-Nonulonic acid
• CAS No.: 153666-19-4
• Molecular Formula: C₉H₁₆O₉
• Molecular Weight: 268.221
• DSSTox Substance ID: DTXSID50661882
• Metabolomics Workbench ID: 71698
• Nikkaji Number: J3.497.427F
• Wikidata: Q27139601
• Mol file: 153666-19-4.mol

Synonyms:2-KDN;2-keto-3-deoxy-D-glycero-D-galacto-nononic acid;2-oxo-3-deoxy-D-glycero-galactononulosonic acid;3-deoxy-D-glycero-D-galacto-2-nonulosonic acid;3-deoxyglycero-galacto-nonulosonic acid;3-deoxyglycerogalacto-2-nonulopyranosonic acid;deoxy-KDN;sialosonic acid;siaX

Chemical Property of Keto-Deoxy-Nonulonic acid

Chemical Property:

• Vapor Pressure: 2.18E-24mmHg at 25°C
• Melting Point: 26-28?C
• Boiling Point: 726.8 °C at 760 mmHg
• PKA: 2.34±0.70(Predicted)
• Flash Point: 285.4 °C
• PSA: 167.91000
• Density: g/cm³
• LogP: -4.01560
• Storage Temp.: −20°C
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 268.07943208
• Heavy Atom Count: 18
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

3-Deoxy-D-glycero-D-galacto-2-nonulosonicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(C(OC1(C(=O)O)O)C(C(CO)O)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H](OC1(C(=O)O)O)[C@@H]([C@@H](CO)O)O)O)O
• Uses: A naturally occuring deaminated sialic acid, exclusively located at the non-reducing end of the sialyl chains. KDN is a sialic acid derivative with potential for anticancer activity. KDN has also been seen to be in elevated levels in human prostate cancer cells.

Technology Process of Keto-Deoxy-Nonulonic acid

There total 7 articles about Keto-Deoxy-Nonulonic acid 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: 86.0%

D-Mannose (530-26-7) + sodium pyruvate (113-24-6) → ketodeoxynonulosonic acid (153666-19-4)

Guidance literature:

With Dyadobacter fermentans N-acetylneuraminate lyase; In aq. buffer; at 37 ℃; for 12h; pH=8; diastereoselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201700678

Reference yield: 43.0%

1-bromo-1,2,3-trideoxy-D-glycero-D-galacto-1-yno-nonitol (1346258-08-9) + acetic acid (64-19-7,77671-22-8) → ketodeoxynonulosonic acid (153666-19-4)

Guidance literature:

With ozone; In dimethylsulfide; water; at 20 ℃; for 1h;

DOI:10.1021/ol202773t

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → ketodeoxynonulosonic acid (153666-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; toluene / 3.25 h / -60 - 0 °C / Reflux; Inert atmosphere

2: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C / Inert atmosphere; Darkness

3: acetic acid / water / 60 h / 40 °C

4: ozone / dimethylsulfide; water / 1 h / 20 °C

With N-Bromosuccinimide; ozone; silver nitrate; acetic acid; In tetrahydrofuran; dimethylsulfide; water; acetone; toluene;

DOI:10.1021/ol202773t

upstream raw materials:

2,3,5,6-di-O-isopropylidene-D-mannofuranose

1,2,3-trideoxy-5,6;8,9-di-O-isopropylidene-D-manno-non-1-yno-4-ulofuranose

1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol

1-bromo-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol

Refernces

Synthesis of fluorescent 4-methyl-7-thiocoumaryl S-glycosides of sialic acid

10.1248/cpb.43.1844

The research focuses on the synthesis of fluorescent 4-methyl-7-thiocoumaryl S-glycosides of sialic acid, which serve as fluorogenic substrates for tracing and quantifying sialidase activity in biological systems. The purpose of this study is to develop new tools for investigating the biological functions of sialic acid in glycoconjugates on bacterial and viral outer membranes. The researchers successfully synthesized three new fluorogenic substrates: 4-methylcoumarin-7-yl S-glycosides of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-D-glucose-D-galacto-2-nonulopyranosonic acid (KDN). They also developed a method for the preparation of a key intermediate, benzyl 5-amino-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosidonic acid (7), which is crucial for the synthesis of N-glycolylneuraminic acid. The synthesis involved various chemicals, including 4-methyl-7-thiocoumarin sodium salt, methyl 5-N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonulopyranosonate, and other related compounds, with the process utilizing Williamson reaction conditions and deprotection steps to yield the final products. The structures of the synthesized materials were confirmed using proton nuclear magnetic resonance (1H-NMR) and carbon-13 nuclear magnetic resonance (13C-NMR) spectroscopy.

Sialyl aldolase in organic synthesis: From the trout egg acid, 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN), to branched-chain higher ketoses as possible new chirons

10.1016/S0040-4020(01)97593-3

This study explores the use of N-acetylneuraminate pyruvate lyase (sialyl aldolase) in organic synthesis. The study demonstrates that sialyl aldolase can catalyze the condensation of pyruvate with various non-nitrogenous sugars, such as D-mannose, to produce ulosonic acids like 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN). The enzyme shows a broad specificity, accepting substrates with different substituents at C(2) provided the D-manno configuration is retained. The authors successfully synthesized several ulosonic acids using immobilized lyase, achieving good yields and demonstrating the potential for scaling up the process. They also explored the enzyme's tolerance to various modifications at different positions of the sugar molecule, revealing its preference for certain configurations and the challenges in using D-arabinose as a substrate.