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Merck
CN

47568

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C11H11FN2O2
CAS Number:
Molecular Weight:
222.22
NACRES:
NA.77
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352202
MDL number:
Beilstein/REAXYS Number:
5052680
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Quality Segment

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

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.


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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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