Carbobenzoxyglycylphenylalanine

Base Information

• Chemical Name: Carbobenzoxyglycylphenylalanine
• CAS No.: 1170-76-9
• Molecular Formula: C19H20 N2 O5
• Molecular Weight: 356.378
• Hs Code.: 2924299090
• European Community (EC) Number: 214-626-9
• DSSTox Substance ID: DTXSID301233120
• Nikkaji Number: J203.429H
• ChEMBL ID: CHEMBL150630
• Mol file: 1170-76-9.mol

Synonyms:carbobenzoxy-Gly-Phe;carbobenzoxyglycyl-L-phenylalanine;carbobenzoxyglycylphenylalanine;carbobenzoxyglycylphenylalanine, (D-Phe)-isomer;Cbz-Gly-Phe

Chemical Property of Carbobenzoxyglycylphenylalanine

Chemical Property:

• Vapor Pressure: 1.43E-17mmHg at 25°C
• Melting Point: 125-126 °C
• Boiling Point: 646 °C at 760 mmHg
• PKA: 3.54±0.10(Predicted)
• Flash Point: 344.5 °C
• PSA: 104.73000
• Density: 1.278 g/cm³
• LogP: 2.50670
• Storage Temp.: -15°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 356.13722174
• Heavy Atom Count: 26
• Complexity: 471

Purity/Quality:

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

Z-Gly-Phe-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CNC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)CNC(=O)OCC2=CC=CC=C2
• Uses: Substrate for carboxypeptidase A.

Technology Process of Carbobenzoxyglycylphenylalanine

There total 72 articles about Carbobenzoxyglycylphenylalanine 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%

Cbz-Gly-ONSuc (2899-60-7) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → Z-Gly-(L)-Phe (1170-76-9)

Guidance literature:

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

Reference yield: 97.0%

Gly-Phe-OH (3321-03-7) + benzyl chloroformate (501-53-1,94274-21-2) → Z-Gly-(L)-Phe (1170-76-9)

Guidance literature:

With sodium carbonate; at 0 - 20 ℃; for 1.33333h;

Reference yield: 93.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + 1--1,2,4-triazolo<4,3-a>pyridinium-3-olate → Z-Gly-(L)-Phe (1170-76-9)

Guidance literature:

With sodium hydroxide; In acetone; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.56.2974

upstream raw materials:

L-phenylalanine

N-benzyloxycarbonyl-thioglycine S-(4-nitro-phenyl ester)

N-(benzyloxycarbonyl)glycyl chloride

H-Phe-OEt

Downstream raw materials:

N-(N-benzyloxycarbonyl-glycyl)-L-thiophenylalanine S-(4-nitro-phenyl ester)

Gly-Phe-OH

ethyl N-benzyloxycarbonylglycyl-L-phenylalanylglycinate

Cbz-glycylphenylalanylglycine

Refernces

• 1、 Paukstelis,J.V.,Kim,M.. "-". . p. 1499 - 1503. Retrieved 1974.
• 2、 Paul,Anderson. "-". . p. 4596,4599. Retrieved 1960.
• 3、 Ezawa, Tetsuya,Jung, Seunghee,Kawashima, Yuya,Noguchi, Takuya,Imai, Nobuyuki. "Convenient green preparation of dipeptides using unprotected α-amino acids". . p. 75 - 83. Retrieved 2017/01/10.
• 4、 Miyazawa, Toshifumi,Horimoto, Takao,Tanaka, Kayoko. "Kinetically controlled peptide synthesis mediated by papain using the carbamoylmethyl ester as an acyl donor". . p. 371 - 376. Retrieved 2014/08/18.