FMOC-TRP(BOC)-OH 25 G

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

Molecular Weight: 526.58. Empirical Formula: C₃₁H₃₀N₂O₆. Quality Level: 300. product line: Novabiochem^®. . Assay: ≥. 90.0% (acidimetric), ≥. 97.5% (HPLC), ≥. 98% (TLC). form: powder. reaction suitability: reaction type: Fmoc solid-phase peptide synthesis. manufacturer/tradename: Novabiochem^®. . application(s): peptide synthesis. functional group: Boc, Fmoc. storage temp.: 15-25°C. InChI: 1S/C31H30N2O6/c1-31(2,3)39-30(37)33-17-19(20-10-8-9-15-27(20)33)16-26(28(34)35)32-29(36)38-18-25-23-13-6-4-11-21(23)22-12-5-7-14-24(22)25/h4-15,17,25-26H,16,18H2,1-3H3,(H,32,36)(H,34,35)/t26-/m0/s1. InChI key: ADOHASQZJSJZBT-SANMLTNESA-N. Storage Class Code: 11 - Combustible Solids. WGK: WGK 3. Flash Point(F): Not applicable. Flash Point(C): Not applicable.