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F0896

Sigma-Aldrich

5-Fluoro-DL-tryptophan

≥95% (HPLC)

Synonym(s):

5-fluoro-tryptophan

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About This Item

Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
154-08-5
Molecular Weight:
222.22
Beilstein:
22753
EC Number:
205-822-5
MDL number:
MFCD00005649
UNSPSC Code:
12352209
PubChem Substance ID:
24894736
NACRES:
NA.26

product name

5-Fluoro-DL-tryptophan, powder or crystals

Assay

≥95% (HPLC)

Quality Level

200

form

powder or crystals

color

slightly off-white to brown

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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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Saswata Sankar Sarkar et al.
The journal of physical chemistry. B, 115(22), 7479-7486 (2011-05-18)
Tryptophan (Trp), an intrinsically fluorescent residue of proteins, has been used widely as an energy donor in fluorescence resonance energy transfer (FRET) experiments aimed at measuring intramolecular distances and distance distributions in protein folding-unfolding reactions. However, the high level of
P M Haggie et al.
The Journal of biological chemistry, 274(7), 3941-3945 (1999-02-06)
The enzymes of the tricarboxylic acid cycle in the mitochondrial matrix are proposed to form a multienzyme complex, in which there is channeling of substrates between enzyme active sites. However no direct evidence has been obtained in vivo for the
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