8.52045

Fmoc-Gln(Trt)-OH

Novabiochem^®

• Synonym(s): Fmoc-Gln(Trt)-OH, N-α-Fmoc-N-γ-trityl-L-glutamine
• Empirical Formula (Hill Notation): C₃₉H₃₄N₂O₅
• CAS Number: 132327-80-1
• Molecular Weight: 610.70
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00077056

Properties

• Quality Segment: 400
• product line: Novabiochem^®
• assay: ≥93.0% (acidimetric), ≥98% (TLC), ≥99.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: 110-125 °C
• application(s): peptide synthesis
• functional group: amide
• storage temp.: -10 to -25°C
• SMILES string: N([C@@H](CCC(=O)NC(c6ccccc6)(c5ccccc5)c4ccccc4)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C39H34N2O5/c42-36(41-39(27-14-4-1-5-15-27,28-16-6-2-7-17-28)29-18-8-3-9-19-29)25-24-35(37(43)44)40-38(45)46-26-34-32-22-12-10-20-30(32)31-21-11-13-23-33(31)34/h1-23,34-35H,24-26H2,(H,40,45)(H,41,42)(H,43,44)/t35-/m0/s1
• InChI key: WDGICUODAOGOMO-DHUJRADRSA-N

Description

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities.
Fmoc-Gln(Trt)-OH 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.

Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] P. Sieber, et al. (1991) Tetrahedron Lett., 32, 739

Application

• Substrate specificity profiling of SARS-CoV-2 Mpro protease provides basis for anti-COVID-19 drug design: This study highlights the use of Fmoc-Gln(Trt)-OH in the synthesis of peptide substrates for biochemical assays, contributing to the development of COVID-19 therapeutics (Rut et al., 2020).

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 160 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.8 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Gln (Trt) -OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Gln(Trt)-Gln(Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Gln-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (GC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (25 mmole in 50 ml DMF): clearly soluble
Assay (acidimetric): ≥ 93.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.02 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1090

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 1