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. The standard derivative for Fmoc SPPS of peptides containing Cys [1]. The Trt group is removed with 95% TFA containing 1-5% TIS. Ideally, this derivative should be introduced using the symmetrical anhydride or DIPCDI/HOBt activation [2,3] to minimize enantiomerization. If activation with uronium or phosphonium reagents, such as HBTU or PyBOP®, is to be employed, it is strongly recommended that collidine is used as the base [4], as this has been shown to significantly reduce loss of optical integrity during coupling.Associated Protocols and Technical ArticlesFmoc-amino acids for Peptide ProductionCleavage and Deprotection Protocols for Fmoc SPPSFmoc SPPS of Cysteine-Containing PeptidesLiterature references[1] S. N. McCurdy (1989) Pept. Res., 2, 147. [2] T. Kaiser, et al. (1996) Tetrahedron Lett., 37, 1187. [3] Y. X. Han, et al. (1997) J. Org. Chem., 62, 4307. [4] Y. N. Angell (2002) J. Peptide Res., 5, 292.
• Application: On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation: Discusses the use of Fmoc-Cys(Trt)-OH in the synthesis of cyclic peptides, highlighting the efficiency of the resin synthesis method. (Serra et al., 2020). Selective Bi‐directional Amide Bond Cleavage of N‐Methylcysteinyl Peptide: The study utilized Fmoc-Cys(Trt)-OH in exploring selective bi-directional amide bond cleavage in peptides, providing insights into controlled peptide modification. (Qiu et al., 2014).
• Linkage: Replaces: 04-12-1018
• Analysis Note: Colour (visual): white to off whiteAppearance of substance (visual): powderColour index (0,5 M in DMF): ≤ 150 HazenIdentity (IR): passes testEnantiomeric purity: ≥ 99.5 % (a/a)Purity (HPLC): ≥ 99.0 % (a/a)Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-ß-Ala-Cys (Trt) -OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Cys(Trt)-Cys(Trt)-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Cys-OH (HPLC): ≤ 0.1 % (a/a)Assay free amino acid (HPLC): ≤ 0.2 %Purity (TLC(011A)): ≥ 98 %Purity (TLC(0811)): ≥ 98 %Solubility (1 mmole in 2 ml DMF): clearly solubleAssay (acidimetric): ≥ 98.0 %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.
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany