(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID Chemical Properties

Melting point:

238-239 °C

Boiling point:

450.7±45.0 °C(Predicted)

Density 

1.442±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.21±0.10(Predicted)

BRN 

5052680

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID Usage And Synthesis

Uses

Exogenous 5-fluoro-Trp is incorporated into proteins in normal protein synthesis. Since ¹⁹F is a useful reporter group, this provides a method for studying enzyme mechanisms by NMR.

Biochem/physiol Actions

5-Fluoro-Trp is nonspecifically cytotoxic. It is believed this is due to malfunctioning enzymes that have had replacements of Trp residues by 5-fluoro-Trp. However, at least one case is known where 5-fluoro-Trp substitution leads to significantly greater catalytic activity.

Purification Methods

Recrystallise it from EtOH, aqueous EtOH or AcOH. Also purify it by passage through a Dowex AG1x2 (acetate form) column and recrystallise the L-enantiomer (from enzymic enrichment) from H2O/EtOH, m 158-163o(dec), [] D -8.3o (c 2.5, N NaOH). [Coy et al. Biochemistry 13 3550 1974, Beilstein 22/14 V 116.]

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