Sigma-Aldrich Fmoc-Trp(Boc)-Oh 25 g

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

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 . 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

P. White in ′Peptides, Chemistry & Biology, Proc. 12th American Peptide Symposium′, J. A. Smith & J. E. Rivier (Eds), ESCOM, Leiden, 1992, PP. 537.
B. Riniker, et Al. (1993)Tetrahedron, 49, 9307.
T. Johnson, et Al. (1993)J. Chem. Soc., Chem. Commun., 369.
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 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.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany