Benzyloxycarbonyltryptophan

Base Information

• Chemical Name: Benzyloxycarbonyltryptophan
• CAS No.: 7432-21-5
• Molecular Formula: C19H18N2O4
• Molecular Weight: 338.363
• Hs Code.: 29339900
• European Community (EC) Number: 231-074-4
• DSSTox Substance ID: DTXSID00225332
• Nikkaji Number: J81.395H
• Wikidata: Q72516522
• ChEMBL ID: CHEMBL291603
• Mol file: 7432-21-5.mol

Synonyms:benzyloxycarbonyl-L-tryptophan;benzyloxycarbonyltryptophan;benzyloxycarbonyltryptophan, monosodium salt;Z-tryptophan

Chemical Property of Benzyloxycarbonyltryptophan

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder powder
• Vapor Pressure: 3.46E-16mmHg at 25°C
• Melting Point: 124-127 °C
• Refractive Index: 1.6140 (estimate)
• Boiling Point: 619.1 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 328.2 °C
• PSA: 91.42000
• Density: 1.341 g/cm³
• LogP: 3.48090
• Storage Temp.: 2-8°C
• Solubility.: methanol: 0.1 g/mL, clear
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 338.12665706
• Heavy Atom Count: 25
• Complexity: 464

Purity/Quality:

99% ^*data from raw suppliers

Z-L-Trp-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O
• Uses: Nα-Cbz-L-tryptophan is an N-Cbz-protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome.

Technology Process of Benzyloxycarbonyltryptophan

There total 22 articles about Benzyloxycarbonyltryptophan 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: 99.0%

benzyl chloroformate (501-53-1,94274-21-2) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-carbobenzyloxy-L-tryptophane (7432-21-5)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2012.09.055

Reference yield: 97.0%

benzyl pyridin-2-yl carbonate (96452-48-1) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-carbobenzyloxy-L-tryptophane (7432-21-5)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 0.3h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 95.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-carbobenzyloxy-L-tryptophane (7432-21-5)

Guidance literature:

With calcium perchlorate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

upstream raw materials:

benzyl chloroformate

L-Tryptophan

N-α-carbobenzoxy-L-tyrosine p-nitrophenyl ester

dibenzyl dicarbonate

Downstream raw materials:

Z-Trp-Gly-Gly-OH

N-carbobenzyloxy-L-tryptophanyl-L-isoleucine methyl ester

S-benzyl-N-(N^α-benzyloxycarbonyl-L-tryptophyl)-L-cystein-ethyl ester

Z-Trp-Gly-OMe

Refernces

• 1、 Huang, Yuanqiong,Liu, Yongxian,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin. "C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids". . p. 462 - 473. Retrieved 2016/01/25.
• 2、 Zur, Arik A.,Chien, Huan-Chieh,Augustyn, Evan,Flint, Andrew,Heeren, Nathan,Finke, Karissa,Hernandez, Christopher,Hansen, Logan,Miller, Sydney,Lin, Lawrence,Giacomini, Kathleen M.,Colas, Claire,Schlessinger, Avner,Thomas, Allen A.. "LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates". supporting information. p. 5000 - 5006. Retrieved 2016/10/05.