Carbobenzoxyphenylalanine

Base Information

• Chemical Name: Carbobenzoxyphenylalanine
• CAS No.: 1161-13-3
• Molecular Formula: C17H17NO4
• Molecular Weight: 299.326
• Hs Code.: 29242990
• European Community (EC) Number: 214-599-3
• DSSTox Substance ID: DTXSID30151276
• Nikkaji Number: J80.209C
• Wikidata: Q72516346
• ChEMBL ID: CHEMBL66143
• Mol file: 1161-13-3.mol

Synonyms:benzyloxycarbonylphenylalanine;carbobenzoxyphenylalanine;carbobenzoxyphenylalanine, (D-Phe)-isomer;carbobenzoxyphenylalanine, (DL-Phe)-isomer;carbobenzoxyphenylalanine, sodium salt, (L-Phe)-isomer;Z-Phe

Chemical Property of Carbobenzoxyphenylalanine

Chemical Property:

• Appearance/Colour: white amorphous powder
• Vapor Pressure: 2.76E-11mmHg at 25°C
• Melting Point: 85-88 °C
• Refractive Index: 5.3 ° (C=4, AcOH)
• Boiling Point: 511.5 °C at 760mmHg
• PKA: 3.86±0.10(Predicted)
• Flash Point: 263.1 °C
• PSA: 75.63000
• Density: 1.248 g/cm³
• LogP: 2.99960
• Storage Temp.: Store at RT.
• Solubility.: DMF (Sparingly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 299.11575802
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

N-(Carbobenzyloxy)-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 62-36/37/38-20/21/22
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2
• Uses: N-Cbz-L-Phenylalanine is used in the synthesis of neurokinin antagonists. Furthermore it is used in the preparation of Co(II), Zn(II), and Cd(II) complexes with N-benzyloxycarbonyl-S-phen ylalanine that displays antimicrobial activity against common strains of bacteria. Inhibitor of thermolysin N-(Carbobenzyloxy)-L-phenylalanine is used in the synthesis of neurokinin antagonists. Furthermore it is used in the preparation of Co(II), Zn(II), and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine that displays antimicrobial activity against common strains of bacteria.

Technology Process of Carbobenzoxyphenylalanine

There total 166 articles about Carbobenzoxyphenylalanine 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-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (2578-84-9) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-Cbz-L-Phe (1161-13-3)

Guidance literature:

With (S)-2-Octanol; borate buffer; water; Bis-(S)-2-octyl sodium sulphosuccinate; 1H-imidazole; In n-heptane; at 25 ℃; Rate constant; k^L; pH= 8.0; other catalyst, other racemic or chiral surfactant and cosurfactants and other proportions of water and surfactant;

DOI:10.1016/S0040-4020(01)89932-4

Reference yield:

benzyl (S)-(1-((4-nitrophenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (14235-15-5,14235-16-6,19647-71-3) → N-Cbz-L-Phe (1161-13-3) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With tris(hydroxymethyl)aminomethane buffer; α-chymotrypsin; In water; acetonitrile; at 25 ℃; pH=8.2; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1021/jo0265075

Reference yield:

DL-Phe/PyS + benzyl chloroformate (501-53-1,94274-21-2) → N-Cbz-L-Phe (1161-13-3) + Cbz-D-Phe (2448-45-5)

Guidance literature:

DL-Phe/PyS; With alpha cyclodextrin; In ethanol; N,N-dimethyl-formamide; at 70 ℃; for 24h;

benzyl chloroformate;

DOI:10.1016/j.tet.2020.131100

upstream raw materials:

(S)-2-(phenylmethoxycarbonyl)amino-1-phenylbut-3-ene

benzyl chloroformate

L-phenylalanine

L-leucine tert-butyl ester

Downstream raw materials:

(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

Cbz-Phe-Gly-OBn

N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester

(S)-benzyl (1-oxo-3-phenyl-1-(phenylamino)propan-2-yl)carbamate

Refernces

• 1、 Millington, Christopher R.,Quarrell, Rachel,Lowe, Gordon. "Aryl hydrazides as linkers for solid phase synthesis which are cleavable under mild oxidative conditions". . p. 7201 - 7204. Retrieved 1998.
• 2、 Mondal, Sahabaj,Haldar, Debasish. "A transient non-covalent hydrogel by a supramolecular gelator with dynamic covalent bonds". . p. 4773 - 4779. Retrieved 2021.
• 3、 West, J. Blair,Scholten, Jeff,Stolowich, N. J.,Hogg, John L.,Scott, A. I.,Wong, Chi-Huey. "Modification of Proteases to Esterases for Peptide Synthesis: Methylchymotrypsin". . p. 3709 - 3710. Retrieved 1988.
• 4、 Ihara, Yasuji,Kunikiyo, Noriko,Kunimasa, Tomoko,Nango, Mamoru,Kuroki, Nobuhiko. "STEREOSELECTIVE MICELLAR CATALYSIS IN THE HYDROLYSIS OF ENANTIOMERIC ESTERS BY DIPEPTIDE DERIVATIVES CONTAINING HISTIDINE RESIDUE". . p. 667 - 670. Retrieved 1981.
• 5、 Heier, Jason L.,Mikolajczak, Dorian J.,B?ttcher, Christoph,Koksch, Beate. "Substrate specificity of an actively assembling amyloid catalyst". . . Retrieved 2017.
• 6、 Blackburn, G. Michael,Kent, Hilary E.,Lilley, Terence H.. "Aqueous Solutions Containing Amino Acids and Peptides. Part 17. --Pairwise Enthalpic Coefficients for the Interaction of N-Acetyl-L-Phenylalaninamide with some N-Acetylamino Acid Amines at 25 deg C". . p. 2207 - 2214. Retrieved 1985.
• 7、 Hattori, Tetsutaro,Kitamoto, Yuichi,Maeda, Tetsuya,Miyoshi, Ikuko,Morohashi, Naoya. "Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin". . . Retrieved 2020/04/01.