47568
5-Fluoro-L-tryptophan
≥98.0% (HPLC)
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关于此项目
经验公式（希尔记法）:
C11H11FN2O2
化学文摘社编号:
分子量:
222.22
NACRES:
NA.77
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352202
MDL number:
Beilstein/REAXYS Number:
5052680
产品名称
5-Fluoro-L-tryptophan, ≥98.0% (HPLC)
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
SMILES string
N[C@@H](Cc1c[nH]c2ccc(F)cc12)C(O)=O
InChI key
INPQIVHQSQUEAJ-VIFPVBQESA-N
assay
≥98.0% (HPLC)
form
powder
optical purity
enantiomeric ratio: ≥99.5:0.5 (HPLC)
mp
270-280 °C
storage temp.
2-8°C
Quality Level
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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.
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.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
N V Visser et al.
FEBS letters, 583(17), 2785-2788 (2009-07-22)
The apoflavodoxin protein from Azotobacter vinelandii harboring three tryptophan (Trp) residues, was biosynthetically labeled with 5-fluorotryptophan (5-FTrp). 5-FTrp has the advantage that chemical differences in its microenvironment can be sensitively visualized via (19)F NMR. Moreover, it shows simpler fluorescence decay
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
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