N2-Acetyl-D-asparagine

Base Information

• Chemical Name: N2-Acetyl-D-asparagine
• CAS No.: 26117-27-1
• Molecular Formula: C6H10N2O4
• Molecular Weight: 174.156
• Hs Code.: 2924199090
• European Community (EC) Number: 247-468-4
• DSSTox Substance ID: DTXSID901314392
• Nikkaji Number: J307.792F
• ChEMBL ID: CHEMBL172478
• Mol file: 26117-27-1.mol

Synonyms:26117-27-1;Nalpha-Acetyl-D-asparagine;N2-Acetyl-D-asparagine;N-ACETYL-D-ASPARAGINE;Ac-D-Asn-OH;Acetyl-D-asparagine;(R)-2-Acetamido-4-amino-4-oxobutanoic acid;(2R)-2-acetamido-4-amino-4-oxobutanoic acid;EINECS 247-468-4;(2R)-3-CARBAMOYL-2-ACETAMIDOPROPANOIC ACID;N|A-Acetyl-D-asparagine;N-alpha-Acetyl-D-asparagine;2-Acetylamino-succinamic acid;CHEMBL172478;SCHEMBL1204312;DTXSID901314392;Nalpha-Acetyl-D-asparagine, ~99%;MFCD00038154;AKOS006240447;AM81556;GS-6064;CS-0204344;EN300-869770;H10522;A818182

Chemical Property of N2-Acetyl-D-asparagine

Chemical Property:

• Vapor Pressure: 2.2E-15mmHg at 25°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
• 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:

99% ^*data from raw suppliers

N-alpha-Acetyl-D-asparagine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

Technology Process of N2-Acetyl-D-asparagine

There total 3 articles about N2-Acetyl-D-asparagine 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:

N-acetylasaparagine (16473-76-0) → L-asparagine (70-47-3,28088-48-4,7006-34-0) + N2-acetyl-D-asparagine (26117-27-1)

Guidance literature:

With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I; at 40 ℃; relative initial rate of hydrolysis;

DOI:10.1021/ja00198a055

Reference yield:

N-acetoxysuccinimide (14464-29-0,57212-69-8) + (R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid (4474-86-6) → N2-acetyl-D-asparagine (26117-27-1)

Guidance literature:

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid; With dmap; 2-(Trimethylsilyl)ethanol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

With palladium 10% on activated carbon; In methanol; dichloromethane;

N-acetoxysuccinimide; Further stages;

Reference yield:

C10H17N3O5 → N2-acetyl-D-asparagine (26117-27-1)

Guidance literature:

With colibactin-activating peptidase; In dimethyl sulfoxide; at 25 ℃; for 5h; pH=8; Enzymatic reaction;

DOI:10.1021/acschembio.9b00069

upstream raw materials:

N-acetylasaparagine

N-acetoxysuccinimide

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

Refernces

• 1、 -. "PRODRUGS OF CYTOTOXIC ACTIVE AGENTS HAVING ENZYMATICALLY CLEAVABLE GROUPS". Paragraph 2296-2298. . Retrieved 2019/03/30.