ChemicalBook > CAS DataBase List > (S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID

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

Product Name
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
CAS No.
16626-02-1
Chemical Name
(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID
Synonyms
L-Trp(5-F)-OH;UNII:5IC9663SHW;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
CBNumber
CB1274150
Molecular Formula
C11H11FN2O2
Formula Weight
222.22
MOL File
16626-02-1.mol
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(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID Property

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
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
F 
10
HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SMB01347
Product name
5-Fluoro-<SC>L</SC>-tryptophan
Purity
≥98% (HPLC)
Packaging
25mg
Price
$149
Updated
2025/07/31
Sigma-Aldrich
Product number
SMB01347
Product name
5-Fluoro-<SC>L</SC>-tryptophan
Purity
≥98% (HPLC)
Packaging
50mg
Price
$227.5
Updated
2025/07/31
Sigma-Aldrich
Product number
47568
Product name
5-Fluoro-L-tryptophan
Purity
≥98.0% (HPLC)
Packaging
25mg
Price
$192
Updated
2025/07/31
Activate Scientific
Product number
AS87334
Product name
5-Fluoro-L-tryptophan
Purity
95+% ee
Packaging
250mg
Price
$236
Updated
2021/12/16
Apolloscientific
Product number
PC530031
Product name
5-Fluoro-L-tryptophan
Purity
97%
Packaging
250mg
Price
$270
Updated
2021/12/16
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(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID Chemical Properties,Usage,Production

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 ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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

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16626-02-1, (S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACIDRelated Search:

Azelaic acid 5-Hydroxymethylfurfural Isoimperatorin Phosphatidylserine Soapnut Extract (-)-Huperzine A L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE 4-Aminobutyric acid Astaxanthin (2S)-2-Amino-3-(6-fluoro-1H-indol-3-yl)propionic acid,(S)-2-AMINO-3-(6-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID (S)-2-AMINO-3-(4-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID 7-CHLORO-L-TRYPTOPHAN (S)-2-AMINO-3-(4-CHLORO-1H-INDOL-3-YL)-PROPIONIC ACID (S)-2-AMINO-3-(5-CHLORO-1H-INDOL-3-YL)-PROPIONIC ACID H-TRP-GLY-OH (2S)-2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid 6-broMo-L-tryptophan H-TRP(BOC)-OH

  • 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
  • (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
  • L-Tryptophan, 5-fluoro-
  • (2S)-2-amino-3-(5-fluoro-1H-indol-3-yl)propanoic acid
  • 5-Fluoro-L-tryptophan >=98.0% (HPLC)
  • Tryptophan Impurity 54
  • 5-fluoro-L-tryptophans
  • L-Trp(5-F)-OH
  • methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoate
  • UNII:5IC9663SHW
  • 16626-02-1
  • C11H11FN2O2H2O
  • Substrate Analogs
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Type
  • Enzyme Inhibitors
  • Biochemicals and Reagents
  • BioChemical
  • Indoles and derivatives
  • FA - FLEnzyme Inhibitors
  • Substrate AnalogsPeptide Synthesis
  • Alphabetic
  • Enzyme Inhibitors by Type
  • F
  • Tryptophan Derivatives
  • Unnatural Amino Acid Derivatives
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