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47568

Sigma-Aldrich

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C11H11FN2O2
Número de CAS:
16626-02-1
Peso molecular:
222.22
Beilstein:
5052680
Número MDL:
MFCD00066470
Código UNSPSC:
12352202
eCl@ss:
32160406
ID de la sustancia en PubChem:
57651014
NACRES:
NA.77

Análisis

≥98.0% (HPLC)

formulario

powder

pureza óptica

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

270-280 °C

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

INPQIVHQSQUEAJ-VIFPVBQESA-N

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Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

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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
Kenji Hamase et al.
Journal of chromatography. A, 1106(1-2), 159-164 (2006-01-31)
A sensitive assay for D-amino-acid oxidase (DAO) activity in mammalian tissues has been established. D-Tryptophan (D-Trp) analogs were tested as substrates for DAO, and 5-fluoro-D-tryptophan (D-FTP) was found to be the best substrate. By the enzymatic reaction, D-FTP was converted
S Rozovsky et al.
Journal of molecular biology, 310(1), 271-280 (2001-06-23)
Product release is partially rate determining in the isomerization reaction catalyzed by Triosephosphate Isomerase, the conversion of dihydroxyacetone phosphate to D-glyceraldehyde 3-phosphate, probably because an active-site loop movement is necessary to free the product from confinement in the active-site. The
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