Fmoc-Gln-OH

Base Information

• Chemical Name: Fmoc-Gln-OH
• CAS No.: 71989-20-3
• Molecular Formula: C20H20N2O5
• Molecular Weight: 368.389
• Hs Code.: 29242990
• European Community (EC) Number: 276-254-3
• DSSTox Substance ID: DTXSID40922737
• Nikkaji Number: J256.558G
• Wikidata: Q72478398
• Mol file: 71989-20-3.mol

Synonyms:N(2)-((9H-fluoren-9-ylmethoxy)carbonyl)-L-glutamine;N(alpha)-fluorenylmethoxycarbonylglutamine;NFMCG

Chemical Property of Fmoc-Gln-OH

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.47E-20mmHg at 25°C
• Melting Point: 220 °C (dec.)(lit.)
• Refractive Index: -18 ° (C=1, DMF)
• 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
• Solubility.: almost transparency in N,N-DMF
• 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% ^*data from raw suppliers

Fmoc-gln ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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-L-glutamine is an N-Fmoc-protected form of L-Glutamine (G597000). L-Glutamine is a non-essential amino acid that is important for cells that proliferate quickly in the body, such as those of the immune system. L-Glutamine is known to be especially important for the gut, as it helps to maintain intestinal structure and function. L-Glutamine also has protective properties against host toxicity of chemotherapy in cancer patients.

Technology Process of Fmoc-Gln-OH

There total 11 articles about Fmoc-Gln-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: 93.0%

L-glutamine (56-85-9,26700-71-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 85.0%

L-glutamine (56-85-9,26700-71-0) + Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester → N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2017.03.021

Reference yield: 83.0%

L-glutamine (56-85-9,26700-71-0) + (9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

upstream raw materials:

L-glutamine

(9-fluorenyl)methyl pentafluorophenyl carbonate

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

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

N_α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid

{1-[2-(4-tert-butoxy-2-{2-[2-(1-hydroxymethyl-2-phenyl-ethylcarbamoyl)-pyrrolidin-1-yl]-1,1-dimethyl-2-oxo-ethylcarbamoyl}-pyrrolidin-1-yl)-1,1-dimethyl-2-oxo-ethylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Refernces

• 1、 Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í. "Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides". . p. 202 - 214. Retrieved 2017/04/06.
• 2、 Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo. "A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids". . p. 10575 - 10582. Retrieved 2013/02/22.