F0896

Sigma-Aldrich

5-Fluoro-DL-tryptophan

powder or crystals

Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
Beilstein/REAXYS Number:
22753
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥95% (HPLC)

form

powder or crystals

application(s)

detection: suitable
peptide synthesis: suitable

color

slightly off-white to brown

mp

265 °C (dec.) (lit.)

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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Packaging

1 g in glass bottle

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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:...
S Rozovsky et al.
Journal of molecular biology, 310(1), 271-280 (2001-06-23)
Product release is partially rate determining in the isomerization reaction catalyzed by Triosephosphate Isomerase, the conversion of dihydroxyacetone phosphate to D-glyceraldehyde 3-phosphate, probably because an active-site loop movement is necessary to free the product from confinement in the active-site. The...
Kenji Hamase et al.
Journal of chromatography. A, 1106(1-2), 159-164 (2006-01-31)
A sensitive assay for D-amino-acid oxidase (DAO) activity in mammalian tissues has been established. D-Tryptophan (D-Trp) analogs were tested as substrates for DAO, and 5-fluoro-D-tryptophan (D-FTP) was found to be the best substrate. By the enzymatic reaction, D-FTP was converted...

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