47568

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

• Empirical Formula (Hill Notation): C₁₁H₁₁FN₂O₂
• CAS Number: 16626-02-1
• Molecular Weight: 222.22
• Beilstein: 5052680
• MDL number: MFCD00066470
• UNSPSC Code: 12352202
• eCl@ss: 32160406
• PubChem Substance ID: 57651014
• NACRES: NA.77

Properties

• Assay: ≥98.0% (HPLC)
• form: powder
• optical purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• mp: 270-280 °C
• storage temp.: 2-8°C
• SMILES string: N[C@@H](Cc1c[nH]c2ccc(F)cc12)C(O)=O
• 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
• InChI key: INPQIVHQSQUEAJ-VIFPVBQESA-N

Description

Application

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves