N-Acetyl-D-tryptophan

Base Information

• Chemical Name: N-Acetyl-D-tryptophan
• CAS No.: 2280-01-5
• Molecular Formula: C13H14 N2 O3
• Molecular Weight: 246.266
• Hs Code.: 2933990090
• European Community (EC) Number: 218-912-4
• DSSTox Substance ID: DTXSID301018144
• Nikkaji Number: J207.900C
• Wikidata: Q27102051
• RXCUI: 1368212
• Metabolomics Workbench ID: 49913
• ChEMBL ID: CHEMBL291829
• Mol file: 2280-01-5.mol

Synonyms:acetyltryptophan;N-acetyl-D-tryptophan;N-acetyltryptophan;N-acetyltryptophanate sodium

Chemical Property of N-Acetyl-D-tryptophan

Chemical Property:

• Melting Point: 186°C
• Boiling Point: 586.6°Cat760mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 308.6°C
• PSA: 82.19000
• Density: 1.33g/cm³
• LogP: 1.69060
• Storage Temp.: −20°C
• Water Solubility.: Practically insoluble in water
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 332

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(=O)N[C@H](CC1=CNC2=CC=CC=C21)C(=O)O
• Uses: N-Acetyl-D-tryptophan is used in preparation of Bordetella petri D-acylated tryptophan hydrolase capable of catalytic hydrolysis of N-acetyl-D-tryptophan to generate D-tryptophan for food, feed and peptide drugs.

Technology Process of N-Acetyl-D-tryptophan

There total 11 articles about N-Acetyl-D-tryptophan 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: 40.0%

acetyltryptophan ethylester (42717-06-6) → N-AcTrp (1218-34-4) + N-acetyl-D-tryptophan (2280-01-5) + N-acetyl-D-tryptophan ethyl ester (92520-19-9)

Guidance literature:

With water; In ethanol; at 25 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Microbiological reaction;

DOI:10.1016/j.tetasy.2010.02.011

Reference yield:

4-nitrophenol acetate (830-03-5) + D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-acetyl-D-tryptophan (2280-01-5)

Guidance literature:

β‐cyclodextrin; In water; dimethyl sulfoxide; at 25 ℃; Rate constant; Mechanism; various conditions, other cyclodextrins (α and γ);

Reference yield:

N-acetyl-DL-tryptophan (1218-34-4,87-32-1) → L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + N-acetyl-D-tryptophan (2280-01-5)

Guidance literature:

beim Behandeln mit einer Amidase in wss. Loesung;

upstream raw materials:

N-acetyl-DL-tryptophan

aniline

AcTrpOMe

(Z)-2-acetamido-3-(3-indolyl)-2-propenoic acid

Downstream raw materials:

D-tryptophan

C₂₄H₂₇N₅O₄

C₃₂H₄₂N₄O₁₀

Refernces

• 1、 Stella, Selvaraj,Chadha, Anju. "Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330". experimental part. p. 457 - 460. Retrieved 2010/06/21.
• 2、 -. "Heat-stable D-aminoacylase". . . Retrieved 2008/06/13.