All Photos(2)
Synonym(s):
5-fluoro-tryptophan
Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
Beilstein:
22753
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26
Recommended Products
Assay
≥95% (HPLC)
Quality Level
form
powder or crystals
color
slightly off-white to brown
mp
265 °C (dec.) (lit.)
application(s)
detection
peptide synthesis
storage temp.
2-8°C
SMILES string
NC(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)
InChI key
INPQIVHQSQUEAJ-UHFFFAOYSA-N
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Related Categories
Application
- Determination of the 19F NMR chemical shielding tensor and crystal structure of 5-fluoro-dl-tryptophan.: This study provides a detailed analysis of the 19F NMR chemical shielding tensor and the crystal structure of 5-Fluoro-dl-tryptophan, offering valuable insights into its electronic environment and molecular interactions. Such detailed structural characterization is crucial for the development of fluorinated drugs and biomolecules, enhancing our understanding of their interactions and functionalities (Sykes BD et al., 2007).
Biochem/physiol Actions
5-Fluoro-DL-tryptophan (5-F-TRP), a fluorine-containing analogue of tryptophan, may be incorporated into proteins such as cyclic AMP receptor protein (CRP) from Escherichia coli to study changes in ligand binding. 5-F-TRP may be used as an internal reference for chromatographic analysis of tryptophan and its derivatives found in whole blood.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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F Sixl et al.
The Biochemical journal, 266(2), 545-552 (1990-03-01)
Two fluorine-containing analogues of the cyclic AMP receptor protein (CRP) from Escherichia coli were prepared by biosynthetic incorporation of 5-fluorotryptophan (5-F-Trp) and 3-fluorotyrosine (3-F-Tyr). The 19F-n.m.r. spectrum of the [5-F-Trp]CRP showed two signals corresponding to the two tryptophan residues, and
N Aymard et al.
Progress in neuro-psychopharmacology & biological psychiatry, 18(1), 77-86 (1994-01-01)
1. 5-Hydroxytryptamine (5-HT) is a well known neurotransmitter implicated in mental disorders, tryptophan (Trp) as amino acid precursor may be interesting. 2. A rapid and simple reversed-phase (mu Bondapac C18 as stationary phase) liquid chromatographic method with fluorimetric detection (excitation:
H Kinoshita et al.
Journal of bioscience and bioengineering, 92(6), 556-559 (2005-10-20)
In our study on nutritional requirement for the hyphal growth of Schizophyllum commune, we found that a Trp- mutant could not grow in the L-Trp-supplied medium in the presence of L-Ser. Further growth studies showed that not only L-Ser but
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
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
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