N-Acetylasparagine

Base Information

• Chemical Name: N-Acetylasparagine
• CAS No.: 4033-40-3
• Molecular Formula: C6H10N2O4
• Molecular Weight: 174.156
• Hs Code.: 2924199090
• European Community (EC) Number: 223-716-7
• UNII: D0P42N84Z6
• DSSTox Substance ID: DTXSID401035921
• Nikkaji Number: J217.850H
• Wikidata: Q27275946
• Metabolomics Workbench ID: 38801
• ChEMBL ID: CHEMBL4778641
• Mol file: 4033-40-3.mol

Synonyms:N-acetyl-L-asparagine;N-acetylasparagine;N-acetylasparagine, (14)C-labeled;N-acetylasparagine, (D)-isomer;N-acetylasparagine, (D,L)-isomer

Chemical Property of N-Acetylasparagine

Chemical Property:

• Vapor Pressure: 2.2E-15mmHg at 25°C
• Melting Point: 168-170 °C
• Refractive Index: 1.508
• Boiling Point: 588.7 °C at 760 mmHg
• PKA: 3.45±0.10(Predicted)
• Flash Point: 309.8 °C
• PSA: 109.49000
• Density: 1.346 g/cm³
• LogP: -0.45770
• Storage Temp.: 2-8°C
• Solubility.: Acetic Acid (Slightly, Heated, Sonicated), DMSO (Slightly), Water (Slightly, Heated)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 174.06405680
• Heavy Atom Count: 12
• Complexity: 214

Purity/Quality:

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

N2-Acetyl-L-asparagine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC(=O)N)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC(=O)N)C(=O)O
• Uses: N2-Acetyl-L-asparagine is a reagent in the synthesis of three mer peptide pENW (pGlu-Asn-Trp) derivatives as antiplatelet aggregation pharmaceuticals.

Technology Process of N-Acetylasparagine

There total 2 articles about N-Acetylasparagine 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:

Fmoc-Asn-OH (71989-16-7) + acetic acid (64-19-7,77671-22-8) → Nα-acetyl-L-asparagine (4033-40-3)

Guidance literature:

Fmoc-Asn-OH; With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Wang resin Inert atmosphere;

acetic acid; With ammonium bicarbonate; In methanol; at 20 ℃; for 3h;

With piperidine; trifluoroacetic acid; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.14233/ajchem.2014.16078

Reference yield:

L-asparagine (70-47-3,28088-48-4,7006-34-0) + 4-nitrophenol acetate (830-03-5) → Nα-acetyl-L-asparagine (4033-40-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 24.84 ℃; pH=8.5 - 9; Kinetics;

DOI:10.1134/S1070363218010127

Reference yield: 46.0%

Nα-acetyl-L-asparagine (4033-40-3) + α-amino-N-(2-phenylethyl)acetamide (62885-88-5) → (N-acetyl-D-asparaginyl)-N-phenethylglycinamide (146429-43-8)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1021/ja00122a001

upstream raw materials:

Fmoc-Asn-OH

acetic acid

L-asparagine

4-nitrophenol acetate

Downstream raw materials:

(N-acetyl-D-asparaginyl)-N-phenethylglycinamide

Ac-L-Asn-L-Ala-OBn

C₁₃H₁₆N₂O₄

L-asparagine

Refernces

• 1、 Zhang,Ruan,Wang,Ruan,Shao,Aalhus,Juárez. "A fundamental study of amadori rearrangement products in reducing sugar-amino acid model system by electrospray ionization mass spectrometry and computation". . p. 2941 - 2944. Retrieved 2014/06/09.