Z-Gly-Gly-Phe-OH

Base Information

• Chemical Name: Z-Gly-Gly-Phe-OH
• CAS No.: 13171-93-2
• Molecular Formula: C21H23 N3 O6
• Molecular Weight: 413.43
• Hs Code.: 2934999090
• NSC Number: 169159
• DSSTox Substance ID: DTXSID70305115
• Mol file: 13171-93-2.mol

Synonyms:Z-Gly-Gly-Phe-OH;13171-93-2;3-phenyl-2-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]propanoic acid;MFCD00055796;(2S)-3-phenyl-2-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]propanoic acid;NSC169159;SCHEMBL16485550;DTXSID70305115;N-Cbz-glycyl-glycyl-L-phenylalanine;AKOS024319363;NSC-169159;SY287573;N-[(benzyloxy)carbonyl]glycylglycylphenylalanine;(11S)-11-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid

Chemical Property of Z-Gly-Gly-Phe-OH

Chemical Property:

• Vapor Pressure: 5.08E-25mmHg at 25°C
• Boiling Point: 771.2 °C at 760 mmHg
• PKA: 3.50±0.10(Predicted)
• Flash Point: 420.2 °C
• PSA: 133.83000
• Density: 1.301 g/cm³
• LogP: 2.01380
• Storage Temp.: -15°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 413.15868546
• Heavy Atom Count: 30
• Complexity: 585

Purity/Quality:

99% ^*data from raw suppliers

(S)-11-Benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)CNC(=O)CNC(=O)OCC2=CC=CC=C2

Technology Process of Z-Gly-Gly-Phe-OH

There total 14 articles about Z-Gly-Gly-Phe-OH 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: 100.0%

C21H22N3O5Pol → N-benzyloxycarbonyl-L-glycyl-L-glycyl-L-phenylalanine (13171-93-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; Resin 002

Reference yield: 58.0%

Cbz-Gly-Gly-OSucc (32943-08-1) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-benzyloxycarbonyl-L-glycyl-L-glycyl-L-phenylalanine (13171-93-2)

Guidance literature:

With TEA; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jm990226g

Reference yield:

CbzGlyGly (2566-19-0) → N-benzyloxycarbonyl-L-glycyl-L-glycyl-L-phenylalanine (13171-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HOBT / CH₂Cl₂

2: 58 percent / TEA / tetrahydrofuran; dimethylformamide; H₂O / 16 h / 20 °C

With TEA; benzotriazol-1-ol; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Condensation / 2: Condensation;

DOI:10.1021/jm990226g

upstream raw materials:

Z-Gly-Gly-L-Phe-OMe

(2S)-amino-4-methylpentanamide hydrochloride

Z-Gly-Gly-L-Phe-OCH₂CF₃

Z-Gly-Gly-L-Phe-OCam

Downstream raw materials:

N-benzyloxycarbonyl-glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

N-Cbz-Gly-Gly-Phe-Leu-OH

glycyl-glycyl-(S)phenylalanyl-(S)leucine methyl ester

[des-tyr¹]-leucine enkephalin

Refernces

• 1、 Singh, Palwinder,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Gurjit,Bhatti, Rajbir. "Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent". . p. 3920 - 3934. Retrieved 2016/05/24.
• 2、 Ganellin, C. Robin,Bishop, Paul B.,Bambal, Ramesh B.,Chan, Suzanne M. T.,Law, James K.,Marabout, Benoit,Luthra, Pratibha Mehta,Moore, Andrew N. J.,Peschard, Olivier,Bourgeat, Pierre,Rose, Christiane,Vargas, Froylan,Schwartz, Jean-Charles. "Inhibitors of tripeptidyl peptidase II. 2. Generation of the first novel lead inhibitor of cholecystokinin-8-inactivating peptidase: A strategy for the design of peptidase inhibitors". . p. 664 - 674. Retrieved 2007/10/03.