Nalpha-Fmoc-Ndelta-trityl-L-glutamine Chemical Properties

Melting point:

165-172 °C

Boiling point:

873.5±65.0 °C(Predicted)

Density 

1.256±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.73±0.10(Predicted)

form 

Powder

color 

White to yellow

optical activity

[α]/D -14.0±1.5°, c = 1% in DMF

Sensitive 

Moisture Sensitive

BRN 

4343953

Major Application

peptide synthesis

InChIKey

WDGICUODAOGOMO-DHUJRADRSA-N

SMILES

C(O)(=O)[C@H](CCC(N)=O)N(C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

132327-80-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-53-43

Safety Statements 

22-24/25-26-61-37-24

WGK Germany 

3

F 

10-21

HS Code 

2924 29 70

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

Nalpha-Fmoc-Ndelta-trityl-L-glutamine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

FMOC-GLN(TRT)-OH, is an amino acid derivative used in chemical synthesis and peptide chemistry.

General Description

Nalpha-Fmoc-Ndelta-trityl-L-glutamine has good solubility properties in most organic solvents, and its use has been shown to result in significantly purer peptides than other derivatives used for the introduction of Gln [1]. Coupling can be performed by standard procedures. The trityl-protecting group is normally removed by 95% TFA in 1-3 hours, with no alkylation of Trp.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

At room temperature, 9- BBN-protected glutamine ( 1 mmol) was stirred vigorously in acetonitrile ( 2 mL), then disodium hydrogen phosphate ( 3 mmol , 426 mg) was added to the resulting reaction solution, and trifluoroperoxyacetic acid ( 6 mL , 0.5 M in CH3CN) was added dropwise to the reaction mixture. The progress of the reaction was determined by TLC and the reaction mixture was allowed to stir until the ingredients were consumed. The reaction was quenched by addition of 20 % Na2SO3 aqueous solution ( 1 m L ). The solvent was removed on a rotary evaporator and the resulting residue was dissolved with dioxane ( 15 mL) and water ( 5 mL) and then treated with solid NaHCO3 ( 5 mmol , 420 mg). The resulting solution was cooled to 0 ??C and 9-fluorenylmethyl-N-succinimidyl carbonate was added to it. The resulting reaction mixture was stirred at a water ice bath temperature for 30 min. the reaction was stirred until the amino acid was completely converted and the volatiles were removed. A further 20 mL of water was added to the reaction solution and the p H of the reaction system was adjusted with 1 M KHSO4 to 3. The aqueous phase was extracted three times with dichloromethane ( 4 ?? 15 mL), and the combined organic extracts were dried with anhydrous Na2SO4, filtered to remove the desiccant and the resulting mixture of organic extracts was concentrated under vacuum. The residue was purified by silica gel column chromatography using dichloromethane/methanol/formic acid (0.1 %) as eluent to give the target product molecule.

Nalpha-Fmoc-Ndelta-trityl-L-glutamine(132327-80-1)Related Product Information

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