Fmoc-D-glutamine

Base Information

• Chemical Name: Fmoc-D-glutamine
• CAS No.: 112898-00-7
• Molecular Formula: C20H20N2O5
• Molecular Weight: 368.389
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID80426320
• Wikidata: Q72478611
• Mol file: 112898-00-7.mol

Synonyms:Fmoc-D-glutamine;Fmoc-D-Gln-OH;112898-00-7;n-alfa-fmoc-d-glutamine;(2R)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid;n-alpha-(9-fluorenylmethyloxycarbonyl)-d-glutamine;n-a-fmoc-d-glutamine;SCHEMBL800090;DTXSID80426320;Fmoc-D-Gln-OH, >=98.0%;MFCD00062959;AKOS016842920;AM81763;CS-W009771;FD21582;AC-17096;AS-49127;EN300-650253;(((9H-fluoren-9-yl)methoxy)carbonyl)-D-glutamine;A802693;J-002863;N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamine;(2R)-4-carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-amino-5-oxopentanoic acid

Chemical Property of Fmoc-D-glutamine

Chemical Property:

• Vapor Pressure: 1.47E-20mmHg at 25°C
• Refractive Index: 1.616
• Boiling Point: 699.8 °C at 760 mmHg
• PKA: 3.73±0.10(Predicted)
• Flash Point: 377.1 °C
• PSA: 118.72000
• Density: 1.332 g/cm³
• LogP: 3.33500
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 368.13722174
• Heavy Atom Count: 27
• Complexity: 545

Purity/Quality:

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

N2-Fmoc-D-glutamine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 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)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CCC(=O)N)C(=O)O
• Uses: N2-Fmoc-D-glutamine is an N-Fmoc-protected form of D-Glutamine (G597295). D-Glutamine is an unnatural isomer of L-Glutamine (G597000) that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells.

Technology Process of Fmoc-D-glutamine

There total 1 articles about Fmoc-D-glutamine 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:

N-Fmoc-glutamine (157355-74-3) → Fmoc-D-Gln-OH (112898-00-7) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3)

Guidance literature:

With chiral column based on 3,5-dimethylphenylcarbamoylated β-cyclodextrin combining cinchona alkaloid immobilized on silica gel; In methanol; formic acid; triethylamine; acetonitrile; at 25 ℃; Reagent/catalyst; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.23237

Reference yield: 82.0%

4-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid (71989-20-3,112898-00-7) + 2,4,5-trichlorophenol (95-95-4) → 4-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2,4,5-trichloro-phenyl ester (82007-10-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 1. 0 deg C, 4h, 2. room temperature;

Reference yield: 64.4%

Fmoc-D-Gln-OH (112898-00-7) + (S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetic acid + (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (101555-63-9,105751-19-7,86069-86-5) → (R)-2-((S)-1-((S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetyl)piperidine-2-carboxamido)pentanediamide

Guidance literature:

Fmoc-D-Gln-OH; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

With 4-methylpiperidin; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h; Sieber amide resin

(S)-2-cyclohexyl-2-(3,4,5-trimethoxyphenyl)acetic acid; (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid; Further stages;

DOI:10.1021/acs.jmedchem.5b01355

upstream raw materials:

N-Fmoc-glutamine

Downstream raw materials:

4-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2,4,5-trichloro-phenyl ester

C₈₈H₁₃₄N₁₂O₁₆S

C₄₄H₇₇N₉O₉

Refernces