(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID Basic information
- Product Name:
- (S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
- Synonyms:
-
- 5-FLUORO-L-TRYPTOPHAN
- 5-FLUORO-L-TRYPTOPHAN MONOHYDRATE
- H-5-FLUORO-TRP-OH H2O
- L-5-FLUOROTRYPTOPHAN
- (S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
- 5-Fluoro-tryptophan monohydrate
- H-L-Trp(5-F)-OH*H2O
- L-5-fluorotryptophan monohydrate
- CAS:
- 16626-02-1
- MF:
- C11H11FN2O2
- MW:
- 222.22
- Product Categories:
-
- Indoles and derivatives
- FA - FLEnzyme Inhibitors
- Substrate AnalogsPeptide Synthesis
- Alphabetic
- Enzyme Inhibitors by Type
- F
- Tryptophan Derivatives
- Unnatural Amino Acid Derivatives
- Novel building
- Mol File:
- 16626-02-1.mol
(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)
- form
- powder
- color
- white
- BRN
- 5052680
- InChI
- 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)/t9-/m0/s1
- InChIKey
- INPQIVHQSQUEAJ-VIFPVBQESA-N
- SMILES
- C(O)(=O)[C@H](CC1C2=C(C=CC(F)=C2)NC=1)N
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.]
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACIDSupplier
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