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 Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature 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.
Linkage
Replaces: 04-12-1103
Analysis Note
Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric 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 soluble
Purity (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
- UPC:
- 41115717
- Condition:
- New
- Weight:
- 1.00 Ounces
- HazmatClass:
- No
- WeightUOM:
- LB
- MPN:
- 8520500100