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 use of this N-in-Boc protected derivative overcomes most of the problems associated with the preparation of Trp containing-peptides by Fmoc SPPS [1]. Cleavage with TFA generates an N-in-carboxy indole which protects the Trp from alkylation [1,2,3] and sulfonation [1,4,5,6,7]. The N-in-carboxy group is removed under aqueous conditions during normal work-up of the peptide. Associated Protocols and Technical ArticlesFmoc-amino acids for Peptide ProductionCleavage and Deprotection Protocols for Fmoc SPPSLiterature references[1] P. White in ′Peptides, Chemistry & Biology, Proc. 12th American Peptide Symposium′, J. A. Smith & J. E. Rivier (Eds), ESCOM, Leiden, 1992, pp. 537. [2] B. Riniker, et al. (1993) Tetrahedron, 49, 9307. [3] T. Johnson, et al. (1993) J. Chem. Soc., Chem. Commun., 369. [4] H. Choi, et al. (1993) Int. J. Peptide Protein Res., 42, 58. [5] C. G. Fields, et al. (1993) Tetrahedron Lett., 34, 6661. [6] T. Lescrinier, et al. (1995) Lett. Pept. Sci., 2, 225. [7] M. Noda & M. Kiffe (1997) J. Peptide Res., 50, 329.
• Application: Highly active antibacterial ferrocenoylated or ruthenocenoylated Arg-Trp peptides can be discovered by an L-to-D substitution scan: Utilizes Fmoc-Trp(Boc)-OH in the synthesis of peptides designed to enhance antibacterial activity, demonstrating its role in the development of new antimicrobial agents (Albada et al., 2014). Nanoparticles generated from a tryptophan derivative: physical characterization and anti-cancer drug delivery: Explores the use of Fmoc-Trp(Boc)-OH in nanoparticle formation for targeted drug delivery systems, particularly in cancer therapy (Dube et al., 2017).
• Linkage: Replaces: 04-12-1103
• 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): ≥ 97.5 % (a/a)Fmoc-ß-Ala-OH (HPLC): ≤ 0.3 % (a/a)Fmoc-ß-Ala-Trp (Boc)-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Trp(Boc)-Trp(Boc)-OH (HPLC): ≤ 0.1 % (a/a)Fmoc-Trp-OH (HPLC): ≤ 1.0 % (a/a)Assay free amino acid (HPLC): ≤ 0.2 %Solubility (25 mmole in 50 ml DMF): clear solublePurity (TLC(011A)): ≥ 98 %Purity (TLC(0811)): ≥ 98 %Assay (acidimetric): ≥ 90.0 %Water (K. F.): ≤ 2.0 %Ethyl acetate (HS-GC): ≤ 2.5 %Acetate (IC): ≤ 0.10 %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