Skip to Content
MilliporeSigma
All Photos(1)

Documents

8.52050

Sigma-Aldrich

Fmoc-Trp(Boc)-OH

Novabiochem®

Synonym(s):

Fmoc-Trp(Boc)-OH, N-α-Fmoc-N-in-t.-Boc-L-tryptophan

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C31H30N2O6
CAS Number:
Molecular Weight:
526.58
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

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

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.

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.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 5

1 of 5

Fmoc-Arg(Pbf)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47349

Fmoc-Arg(Pbf)-OH

Fmoc-Arg(Pbf)-OH Novabiochem®

Sigma-Aldrich

8.52067

Fmoc-Arg(Pbf)-OH

Fmoc-Phg-OH ≥98.0% (HPLC)

Sigma-Aldrich

47531

Fmoc-Phg-OH

Fmoc-Ala-OH Novabiochem®

Sigma-Aldrich

8.52003

Fmoc-Ala-OH

Fmoc-Thr(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47622

Fmoc-Thr(tBu)-OH

Related Content

Purer Fmocs Means Purer Peptides

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service