| Identification | Back Directory | [Name]
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID | [CAS]
16626-02-1 | [Synonyms]
H-L-Trp(5-F)-OH*H2O
L-5-FLUOROTRYPTOPHAN
5-FLUORO-L-TRYPTOPHAN
H-5-FLUORO-TRP-OH H2O
Tryptophan Impurity 54
5-fluoro-L-tryptophans
L-Tryptophan, 5-fluoro-
5-Fluoro-tryptophan monohydrate
L-5-fluorotryptophan monohydrate
5-FLUORO-L-TRYPTOPHAN MONOHYDRATE
5-Fluoro-L-tryptophan >=98.0% (HPLC)
(S)-5-Fluoro-α-amino-1H-indole-3-propionic acid
(S)-α-Amino-5-fluoro-1H-indole-3-propionic acid
(S)-2-AMino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
(2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid | [Molecular Formula]
C11H11FN2O2 | [MDL Number]
MFCD00066470 | [MOL File]
16626-02-1.mol | [Molecular Weight]
222.22 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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