F7376
4-Fluoro-DL-tryptophan
crystalline
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About This Item
Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
assay
≥98.0% (TLC)
form
crystalline
technique(s)
NMR: suitable
color
off-white
storage temp.
−20°C
SMILES string
NC(Cc1c[nH]c2cccc(F)c12)C(O)=O
InChI
1S/C11H11FN2O2/c12-7-2-1-3-9-10(7)6(5-14-9)4-8(13)11(15)16/h1-3,5,8,14H,4,13H2,(H,15,16)
InChI key
DEBQMEYEKKWIKC-UHFFFAOYSA-N
Biochem/physiol Actions
4-Fluoro-DL-tryptophan (4-F-TRP) is used to label bacterial arginyl-tRNA synthetases for conformational analysis and to label myoglobins and hemoglobins for NMR spectra analysis.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Q S Zhang et al.
Journal of protein chemistry, 18(2), 187-192 (1999-05-20)
Escherichia coli 4-fluorotryptophan-substituted arginyl-tRNA synthetase was biosynthetically prepared and purified from a tryptophan auxotroph which could overproduce this enzyme. A method was developed to separate 4-fluorotryptophan from tryptophan and to determine accurately their contents in the 4-fluorotryptophan-containing proteins. It was
J M Bacher et al.
Journal of bacteriology, 183(18), 5414-5425 (2001-08-22)
Escherichia coli isolates that were tolerant of incorporation of high proportions of 4-fluorotryptophan were evolved by serial growth. The resultant strain still preferred tryptophan for growth but showed improved growth relative to the parental strain on other tryptophan analogues. Evolved
B Delagoutte et al.
The EMBO journal, 19(21), 5599-5610 (2000-11-04)
The 2.2 A crystal structure of a ternary complex formed by yeast arginyl-tRNA synthetase and its cognate tRNA(Arg) in the presence of the L-arginine substrate highlights new atomic features used for specific substrate recognition. This first example of an active
Yong-Neng Yao et al.
FEBS letters, 547(1-3), 197-200 (2003-07-16)
The 19F nuclear magnetic resonance (NMR) spectra of 4-fluorotryptophan (4-F-Trp)-labeled Escherichia coli arginyl-tRNA synthetase (ArgRS) show that there are distinct conformational changes in the catalytic core and tRNA anticodon stem and loop-binding domain of the enzyme, when arginine and tRNA(Arg)
J L Hott et al.
The Biochemical journal, 264(1), 297-299 (1989-11-15)
The derivative 4-fluorotryptophan was confirmed to have negligible fluorescence at 25 degrees C and 285 nm (tryptophan/4-fluorotryptophan quantum-yield ratio greater than 100:1). However, photolysis experiments on tryptophan and 4-fluorotryptophan, in which loss of starting material was measured by reverse-phase h.p.l.c.
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