Fmoc-L-glutamine 4-nitrophenyl ester

Base Information

• Chemical Name: Fmoc-L-glutamine 4-nitrophenyl ester
• CAS No.: 71989-21-4
• Molecular Formula: C26H23 N3 O7
• Molecular Weight: 489.48
• DSSTox Substance ID: DTXSID50548947
• Wikidata: Q72478427
• Mol file: 71989-21-4.mol

Synonyms:71989-21-4;Fmoc-L-glutamine 4-nitrophenyl ester;Fmoc-Gln-ONp;(4-nitrophenyl) (2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoate;(S)-4-Nitrophenyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoate;DTXSID50548947;AKOS024386389;N-[(9H-Fluoren-9-ylmethoxy)-carbonyl]-glutamine 4-nitrophenyl ester;4-Nitrophenyl N~2~-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-glutaminate;(S)-4-nitrophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-amino-5-oxopentanoate;(S)-4-Nitrophenyl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoate

Chemical Property of Fmoc-L-glutamine 4-nitrophenyl ester

Chemical Property:

• PSA: 153.54000
• Density: 1.362
• LogP: 5.28740
• Storage Temp.: 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 489.15360008
• Heavy Atom Count: 36
• Complexity: 786

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-L-glutamine 4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCC(=O)N)C(=O)OC4=CC=C(C=C4)[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CCC(=O)N)C(=O)OC4=CC=C(C=C4)[N+](=O)[O-]

Technology Process of Fmoc-L-glutamine 4-nitrophenyl ester

There total 1 articles about Fmoc-L-glutamine 4-nitrophenyl ester 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: 51.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) → Nα-fluorenylmethoxycarbonyl-L-glutamine p-nitrophenyl ester (71989-21-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1039/P19810000538

Reference yield:

Nα-fluorenylmethoxycarbonyl-L-glutamine p-nitrophenyl ester (71989-21-4) → (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-((R)-3-Amino-2-oxo-pyrrolidin-1-yl)-4-methyl-pentanoylamino]-4-methylsulfanyl-butyrylamino}-4-carbamoyl-butyrylamino)-3-phenyl-propionylamino]-3-phenyl-propionyl azide

Guidance literature:

Multi-step reaction with 2 steps

2: 7.2 M HCL, isopentyl nitrite / dimethylformamide; tetrahydrofuran / 3.5 h / -25 °C

With hydrogenchloride; isopentyl nitrite; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00053a001

Reference yield:

Nα-fluorenylmethoxycarbonyl-L-glutamine p-nitrophenyl ester (71989-21-4) + (Fmoc-Phe-O)2O (75530-96-0) + (2S)-2-<(3R)-3-<(tert-butoxycarbonyl)amino>-2-oxopyrrolidin-1-yl>-4-methylpentanoic acid (82611-48-1) + C40H40N2O7S2 → (S)-2-{(S)-2-[(S)-2-((R)-3-Amino-2-oxo-pyrrolidin-1-yl)-4-methyl-pentanoylamino]-4-methylsulfanyl-butyrylamino}-pentanedioic acid 5-amide 1-{[(S)-1-((S)-1-hydrazinocarbonyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-amide}

Guidance literature:

Multistep reaction;

DOI:10.1021/jm00053a001

upstream raw materials:

4-nitro-phenol

N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

Refernces

• 1、 Bodanszky, Agnes,Bodanszky, Miklos,Chandramouli, Nagarajan,Kwei, Joseph Z.,Martinez, Jean,Tolle, John C.. "Active Esters of 9-Fluorenylmethyloxycarbonyl Amino Acids and Their Application in the Stepwise Lengthening of a Peptide Chain". . p. 72 - 76. Retrieved 2007/10/02.