N-CBZ-D-PHE-PHE-GLY

Base Information

• Chemical Name: N-CBZ-D-PHE-PHE-GLY
• CAS No.: 75539-79-6
• Molecular Formula: C28H29 N3 O6
• Molecular Weight: 503.555
• Mol file: 75539-79-6.mol

Synonyms:Glycine,N-[N-[N-[(phenylmethoxy)carbonyl]-D-phenylalanyl]-L-phenylalanyl]-

Chemical Property of N-CBZ-D-PHE-PHE-GLY

Chemical Property:

• Vapor Pressure: 1.28E-31mmHg at 25°C
• Boiling Point: 861.2°C at 760 mmHg
• Flash Point: 474.6°C
• PSA: 133.83000
• Density: 1.273g/cm³
• LogP: 3.62510
• Storage Temp.: −20°C

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of N-CBZ-D-PHE-PHE-GLY

There total 4 articles about N-CBZ-D-PHE-PHE-GLY 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: 77.0%

(S)-PheGly (721-90-4) + (R)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid benzotriazol-1-yl ester (26055-07-2) → benzyloxycarbonyl-D-Phe-Phe-Gly (75539-79-6)

Guidance literature:

With benzyltrimethylammonium chloride; In chloroform; for 3h; Ambient temperature;

DOI:10.1039/c39900001045

Reference yield:

1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine (2644-64-6,2797-68-4) + bee-venom phospholipase A2 + 1-palmitoyl-2-(Cbz-D-Phe-Phe-Gly)-sn-glycero-3-phosphocholine → 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5) + benzyloxycarbonyl-D-Phe-Phe-Gly (75539-79-6)

Guidance literature:

1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine; 1-palmitoyl-2-(Cbz-D-Phe-Phe-Gly)-sn-glycero-3-phosphocholine; With calcium chloride; In aq. buffer; at 40 ℃; for 0.25h; pH=8.5;

bee-venom phospholipase A₂; In aq. buffer; at 40 ℃; for 1.5h; pH=8.5; Enzymatic reaction;

DOI:10.1016/j.chemphyslip.2014.06.001

Reference yield:

Cbz-D-Phe (2448-45-5) + Fmoc-Gly-OPfp (86060-85-7) + N-α-Fmoc-L-phenylalanine pentafluorophenyl ester (86060-92-6,159505-85-8) → benzyloxycarbonyl-D-Phe-Phe-Gly (75539-79-6)

Guidance literature:

Yield given. Multistep reaction; solid phase synthesis;

DOI:10.1016/S0040-4039(00)92110-5

upstream raw materials:

(S)-PheGly

(R)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid benzotriazol-1-yl ester

Cbz-D-Phe

Fmoc-Gly-OPfp

Refernces

Incorporation of Aerobic Oxygen into the Hydroxyglycyl Intermediate during Formation of C-Terminal Peptide Amides by Peptidylglycine α-Amidating Monooxygenase (PAM)

10.1039/c39910000571

The research investigates the mechanism of how peptidylglycine α-amidating monooxygenase (PAM) incorporates oxygen into the hydroxyglycyl intermediate during the formation of C-terminal peptide amides. The purpose is to determine whether the hydroxy group in the intermediate is formed by direct hydroxylation of carbon or via oxidative formation of an N-acyl imine followed by addition of water. The key chemicals used include D-phenylalanyl-L-phenylalanylglycine as the substrate, PAM enzyme, ascorbate, copper, molecular oxygen, and 18O2 for labeling. The study concludes that aerobic oxygen is the primary source of the hydroxy group, supporting the direct hydroxylation mechanism, as evidenced by the 30% 18O incorporation into the hydroxy group of the product when 18O2 was used in the reaction.