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Key Documents

F7626

Sigma-Aldrich

6-Fluoro-DL-tryptophan

crystalline

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About This Item

Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

form

crystalline

mp

280-285 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

NC(Cc1c[nH]c2cc(F)ccc12)C(O)=O

InChI

1S/C11H11FN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)

InChI key

YMEXGEAJNZRQEH-UHFFFAOYSA-N

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Application

6-Fluoro-DL-tryptophan (6-F-TRP), a serotonin (5-HT) synthesis inhibitor, is metabolized in the brain and may be useful for tracing neuronal serotoninergic pools. 6-F-TRP is used as a competitive inhibitor of tryptophan binding to albumin and passage through the blood brain barrier (BBB).

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

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Albumin binding and brain uptake of 6-fluoro-DL-tryptophan: competition with L-tryptophan.
Chanut E, Zini R, Trouvin JH, Riant P, et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 44, 2082-2085 (1992)
A H Baugher et al.
Biophysical journal, 75(5), 2574-2576 (1998-10-28)
Rotational-echo double-resonance (REDOR) 13C NMR spectra (with 19F dephasing) have been obtained of 6-fluorotryptophan complexed by a polymeric amphiphilic nanosphere consisting of a polystyrene core covalently attached to a poly(acrylic acid)-polyacrylamide shell. The REDOR spectra show that aromatic carbons from
F Richard et al.
Brain research, 536(1-2), 41-45 (1990-12-17)
An immunoblot procedure was developed to quantify the amount of tryptophan hydroxylase (TpOH), the rate limiting enzyme in the synthesis of serotonin, in the rat raphe dorsalis nucleus (NRD). Using this method we have studied the time course variations in
Induction of anthranilate synthase activity by elicitors in oats.
Matsukawa T, Ishihara A, Iwamura H.
Zeitschrift fur Naturforschung, 57, 121-128 (2002)
E Li et al.
The Journal of biological chemistry, 264(29), 17041-17048 (1989-10-15)
Rat cellular retinol-binding protein II (CRBP II) is a 15.6-kDa intestinal protein which binds all-trans-retinol and all-trans-retinal but not all-trans-retinoic acid. We have previously analyzed the interaction of Escherichia coli-derived rat apoCRBP II with several retinoids using fluorescence spectroscopic techniques.

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