Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

47568

Sigma-Aldrich

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
16626-02-1
Molecular Weight:
222.22
Beilstein:
5052680
MDL number:
MFCD00066470
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
57651014
NACRES:
NA.77

Assay

≥98.0% (HPLC)

form

powder

optical purity

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

270-280 °C

storage temp.

2-8°C

SMILES string

N[C@@H](Cc1c[nH]c2ccc(F)cc12)C(O)=O

InChI

1S/C11H11FN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1

InChI key

INPQIVHQSQUEAJ-VIFPVBQESA-N

Looking for similar products? Visit Product Comparison Guide

Application

Exogenous 5-fluoro-Trp is incorporated into proteins in normal protein synthesis. Since 19F is a useful reporter group, this provides a method for studying enzyme mechanisms by NMR.

Biochem/physiol Actions

5-Fluoro-Trp is nonspecifically cytotoxic. It is believed this is due to malfunctioning enzymes that have had replacements of Trp residues by 5-fluoro-Trp. However, at least one case is known where 5-fluoro-Trp substitution leads to significantly greater catalytic activity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

G S Rule et al.
Biochemistry, 26(2), 549-556 (1987-01-27)
In this study we demonstrate the potential of combining fluorine-19 nuclear magnetic resonance (NMR) spectroscopy with molecular genetics. We are using the membrane-bound enzyme D-lactate dehydrogenase of Escherichia coli as a model system to characterize interactions between proteins and lipids.
E W Miles et al.
Biochemistry, 25(15), 4240-4249 (1986-07-29)
We are exploring the active site and the mechanism of the pyridoxal phosphate dependent reactions of the bacterial tryptophan synthase alpha 2 beta 2 complex by use of substrate analogues and of reaction intermediate analogues. Fluorine-19 nuclear magnetic resonance studies
Dereje Abate Negatu et al.
mBio, 10(2) (2019-03-28)
Indole propionic acid (IPA), produced by the gut microbiota, is active against Mycobacterium tuberculosisin vitro and in vivo However, its mechanism of action is unknown. IPA is the deamination product of tryptophan (Trp) and thus a close structural analog of
Dmitri Toptygin et al.
The journal of physical chemistry. B, 110(51), 26292-26302 (2006-12-22)
The B1 domain of Streptococcal protein G (GB1) is a small, thermostable protein containing a single tryptophan residue. We recorded time-resolved fluorescence of the wild-type GB1 and its 5-fluorotryptophan (5FTrp) variant at more than 30 emission wavelengths between 300 and
Milena Opačić et al.
Biochimica et biophysica acta, 1818(3), 861-868 (2011-11-22)
The mannitol transporter EII(mtl) from Escherichia coli is responsible for the uptake of mannitol over the inner membrane and its concomitant phosphorylation. EII(mtl) is functional as a dimer and its membrane-embedded C domain, IIC(mtl), harbors one high affinity mannitol binding
View All Related Papers

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