N-Acetyl-L-tryptophan ethyl ester

Base Information

• Chemical Name: N-Acetyl-L-tryptophan ethyl ester
• CAS No.: 2382-80-1
• Deprecated CAS: 17002-30-1,27442-41-7,27442-71-3,37784-18-2,685861-09-0
• Molecular Formula: C15H18 N2 O3
• Molecular Weight: 274.32
• Hs Code.: 29339900
• European Community (EC) Number: 219-190-3
• UNII: 3779MVZ8JX
• Nikkaji Number: J207.901A
• Wikidata: Q27256647
• Mol file: 2382-80-1.mol

Synonyms:Ac-Trp-OEt;2382-80-1;N-Acetyl-L-tryptophan ethyl ester;Ethyl N-acetyl-L-tryptophanate;Acetyl-L-tryptophan ethyl ester;L-Tryptophan, N-acetyl-, ethyl ester;ethyl (2S)-2-acetamido-3-(1H-indol-3-yl)propanoate;UNII-3779MVZ8JX;3779MVZ8JX;C15H18N2O3;EINECS 219-190-3;(S)-Ethyl 2-acetamido-3-(1H-indol-3-yl)propanoate;Ac-L-Trp-OEt;Ethyl 2-(acetylamino)-3-(1H-indol-3-yl)propanoate #;Ethyl acetyl-L-tryptophanate;SCHEMBL3185689;KQGQONPKSKUHHT-AWEZNQCLSA-N;N_Acetyl_L_tryptophan_ethyl_ester;MFCD00005643;N-ACETYLTRYPTOPHAN ETHYL ESTER;AKOS015838772;AKOS015898362;CS-W012333;N-ACETYLTRYPTOPHAN O-ETHYL ESTER;DS-16119;N-Acetyl-L-tryptophan ethyl ester, 99%;A0122;N.ALPHA.-ACETYL-L-TRYPTOPHAN ETHYL ESTER;TRYPTOPHAN, N-ACETYL-, ETHYL ESTER, L-;A816927;J-015232;N-Acetyl-L-tryptophan ethyl ester (Ac-L-Trp-OEt);Q27256647;(2S)-2-acetamido-3-(1H-indol-3-yl)propanoic acid ethyl ester

Chemical Property of N-Acetyl-L-tryptophan ethyl ester

Chemical Property:

• Appearance/Colour: white to slightly cream crystalline powder
• Vapor Pressure: 8.12E-11mmHg at 25°C
• Melting Point: 112-114 °C(lit.)
• Refractive Index: 6.5 ° (C=2, EtOH)
• Boiling Point: 515.1°Cat760mmHg
• PKA: 14.82±0.46(Predicted)
• Flash Point: 265.3°C
• PSA: 71.19000
• Density: 1.215g/cm³
• LogP: 2.16910
• Storage Temp.: -15°C
• Solubility.: soluble in Methanol
• Water Solubility.: 1.47g/L(28 oC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 274.13174244
• Heavy Atom Count: 20
• Complexity: 359

Purity/Quality:

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

N-alpha-Acetyl-L-tryptophan ethyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C
• Isomeric SMILES: CCOC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)C
• Uses: Substrate for chymotrypsin and carboxypeptidase Y.

Technology Process of N-Acetyl-L-tryptophan ethyl ester

There total 9 articles about N-Acetyl-L-tryptophan ethyl ester 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%

ethanol (64-17-5) + N-AcTrp (1218-34-4) → N-acetyl-L-tryptophane ethyl ester (2382-80-1)

Guidance literature:

lipoglycosylated α-chymotrypsin; In chloroform; at 30 ℃; or other solvents;

DOI:10.1016/0040-4039(90)80090-9

Reference yield: 54.0%

L-tryptophan ethyl ester hydrochloride (2899-28-7,6519-67-1,61535-49-7,67557-18-0,68401-14-9) + acetic anhydride (108-24-7) → N-acetyl-L-tryptophane ethyl ester (2382-80-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/tx5001656

Reference yield:

tryptophan ethyl ester hydrochloride salt + ethyl acetate (141-78-6) → N-acetyl-L-tryptophane ethyl ester (2382-80-1)

Guidance literature:

With triethylamine; at 5 - 20 ℃; for 1h;

upstream raw materials:

ethanol

N-AcTrp

N^α-acetyl-2,3-dihydro-L-tryptophan ethyl ester

acetic anhydride

Downstream raw materials:

N-AcTrp

Ac-Trp-Phe-NH₂

N^α-acetyl-L-tryptophan-amide

Refernces

• 1、 Kise, Hideo,Shirato, Hitoshi. "SYNTHESIS OF AROMATIC AMINO ACID ETHYL ESTERS BY α-CHYMOTRYPSIN IN SOLUTIONS OF HIGH ETHANOL CONCENTRATIONS". . p. 6081 - 6084. Retrieved 1985.
• 2、 Karlsson, Isabella,Persson, Elin,Ekebergh, Andreas,M?rtensson, Jerker,B?rje, Anna. "Ketoprofen-induced formation of amino acid photoadducts: Possible explanation for photocontact allergy to ketoprofen". . p. 1294 - 1303. Retrieved 2014/08/05.
• 3、 Peissker, Fabian,Fischer, Lutz. "Crosslinking of imprinted proteases to maintain a tailor-made substrate selectivity in aqueous solutions". . p. 2231 - 2237. Retrieved 2007/10/03.