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47568

Sigma-Aldrich

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

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About This Item

Formule empirique (notation de Hill):
C11H11FN2O2
Numéro CAS:
16626-02-1
Poids moléculaire :
222.22
Numéro Beilstein :
5052680
Numéro MDL:
MFCD00066470
Code UNSPSC :
12352202
eCl@ss :
32160406
ID de substance PubChem :
57651014
Nomenclature NACRES :
NA.77

Pureté

≥98.0% (HPLC)

Forme

powder

Pureté optique

enantiomeric ratio: ≥99.5:0.5 (HPLC)

Pf

270-280 °C

Température de stockage

2-8°C

Chaîne 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

Clé InChI

INPQIVHQSQUEAJ-VIFPVBQESA-N

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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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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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.
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
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
Warintra Pitsawong et al.
eLife, 7 (2018-06-15)
Protein kinases are major drug targets, but the development of highly-selective inhibitors has been challenging due to the similarity of their active sites. The observation of distinct structural states of the fully-conserved Asp-Phe-Gly (DFG) loop has put the concept of
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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