Fmoc-L-phenylalanine

Base Information

• Chemical Name: Fmoc-L-phenylalanine
• CAS No.: 35661-40-6
• Molecular Formula: C24H21NO4
• Molecular Weight: 387.435
• Hs Code.: 2924 29 70
• European Community (EC) Number: 252-661-1
• DSSTox Substance ID: DTXSID30951314
• Nikkaji Number: J256.551J
• Wikidata: Q82929582
• ChEMBL ID: CHEMBL357583
• Mol file: 35661-40-6.mol

Synonyms:fluorenylmethoxycarbonyl-conjugated phenylalanine;Fmoc-Phe;Fmoc-phenylalanine

Chemical Property of Fmoc-L-phenylalanine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.07E-16mmHg at 25°C
• Melting Point: 180-187 °C(lit.)
• Refractive Index: -39.5 ° (C=1, DMF)
• Boiling Point: 620.1 °C at 760 mmHg
• PKA: 3.77±0.10(Predicted)
• Flash Point: 328.8 °C
• PSA: 75.63000
• Density: 1.276 g/cm³
• LogP: 4.61190
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMF (Sparingly, Sonicated), DMSO (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 387.14705815
• Heavy Atom Count: 29
• Complexity: 551

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-L-Phe ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: (Fmoc-Phe-OH) L-Phenylalanine (P319415) derivative, used in the preparation of peptides and deltorphin derivatives. A potential inhibitor of IGF-I and IGF-Binding Protein-5 complex.

Technology Process of Fmoc-L-phenylalanine

There total 54 articles about Fmoc-L-phenylalanine 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%

methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-phenylalaninate (129397-81-5) → N-Fmoc L-Phe (35661-40-6)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 0.25h; chemoselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1002/chem.201501799

Reference yield: 98.0%

ethyl (S)-N-α-(fluorenylmethyloxycarbonyl)-phenylalaninate → N-Fmoc L-Phe (35661-40-6)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 0.5h; Reagent/catalyst; Solvent; Concentration; chemoselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1002/chem.201501799

Reference yield: 96.0%

(S)-2-(9H-fluoren-9-ylmethoxycarbonyl-amino)-3-phenyl-propionic acid benzyl ester → N-Fmoc L-Phe (35661-40-6)

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 120 ℃; for 0.25h; chemoselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1002/chem.201501799

upstream raw materials:

L-phenylalanine

(fluorenylmethoxy)carbonyl chloride

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

1,2,2,2-Tetrachloroethyl 9-fluorenylmethyl carbonate

Downstream raw materials:

N-α-Fmoc-L-phenylalanine pentafluorophenyl ester

H-Tyr-Orn[*]-Phe-Asp[*]-NH₂

H-Tyr-D-Asp[*]-Phe-A₂bu[*]-NH₂

H-Tyr-D-Orn[*]-Phe-D-Asp[*]-NH₂

Refernces

• 1、 Misra, Souvik,Mukherjee, Soumyajit,Ghosh, Anamika,Singh, Pijush,Mondal, Sanjoy,Ray, Debes,Bhattacharya, Gourav,Ganguly, Debabani,Ghosh, Alok,Aswal,Mahapatra, Ajit K.,Satpati, Biswarup,Nanda, Jayanta. "Single Amino-Acid Based Self-Assembled Biomaterials with Potent Antimicrobial Activity". . p. 16744 - 16753. Retrieved 2021/10/25.
• 2、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.