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-Asn(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 Asn [1,2]. Coupling can be performed by standard procedures. The trityl group is normally removed by 95% TFA in 1-3 hours, with no alkylation of Trp residues. When Asn(Trt) is the N-terminal residue, the reaction time may need to be extended to ensure complete deprotection [3]. Associated Protocols and Technical ArticlesFmoc-amino acids for Peptide ProductionCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] P. Sieber, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium′, R. Epton (Eds), SPCC UK Ltd., Birmingham, 1990, pp. 577. [2] P. Sieber, et al. (1991) Tetrahedron Lett., 32, 739. [3] M. Friede, et al. (1992) Pept. Res., 5, 145.
• Application: Synthesis of a burkholdine analogue containing β-hydroxytyrosine: This study discusses the synthesis of a burkholdine analogue, utilizing Fmoc-Asn(Trt)-OH as part of the solid support loading process (Kato et al., 2019).
• Linkage: Replaces: 04-12-1089
• Analysis Note: Colour (visual): white to off whiteAppearance of substance (visual): powderColour index (0,5 M in DMF): ≤ 150 HazenIdentity (IR): passes testEnantiomeric purity: ≥ 99.7 % (a/a)Purity (HPLC): ≥ 99.0 % (a/a)Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-ß-Ala-Asn (Trt)-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Asn(Trt)-Asn(Trt)-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Asn-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 solubleAssay (acidimetric): ≥ 98.0 %Water (K. F.): ≤ 2.0 %Ethyl acetate (HS-GC): ≤ 0.5 %Acetate (IC): ≤ 0.05 %To see the solvent systems used for TLC of Novabiochem® products please click here.
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany