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ChemicalBook--->CAS DataBase List--->16626-02-1

16626-02-1

16626-02-1 Structure

16626-02-1 Structure
IdentificationBack 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 PropertiesBack 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
[form ]

powder
[pka]

2.21±0.10(Predicted)
[color ]

white
[BRN ]

5052680
Safety DataBack Directory
[Safety Statements ]

22-24/25
[WGK Germany ]

3
[F ]

10
[HS Code ]

2933998090
Hazard InformationBack 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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