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Merck
CN

47568

Sigma-Aldrich

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

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关于此项目

经验公式(希尔记法):
C11H11FN2O2
CAS Number:
分子量:
222.22
Beilstein:
5052680
MDL编号:
UNSPSC代码:
12352202
eCl@ss:
32160406
PubChem化学物质编号:
NACRES:
NA.77
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质量水平

方案

≥98.0% (HPLC)

表单

powder

光学纯度

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

270-280 °C

储存温度

2-8°C

SMILES字符串

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

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应用

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.

生化/生理作用

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Dereje Abate Negatu et al.
mBio, 10(2) (2019-03-28)
Indole propionic acid (IPA), produced by the gut microbiota, is active against Mycobacterium tuberculosisin vitro and in vivo However, its mechanism of action is unknown. IPA is the deamination product of tryptophan (Trp) and thus a close structural analog of
G S Rule et al.
Biochemistry, 26(2), 549-556 (1987-01-27)
In this study we demonstrate the potential of combining fluorine-19 nuclear magnetic resonance (NMR) spectroscopy with molecular genetics. We are using the membrane-bound enzyme D-lactate dehydrogenase of Escherichia coli as a model system to characterize interactions between proteins and lipids.
E W Miles et al.
Biochemistry, 25(15), 4240-4249 (1986-07-29)
We are exploring the active site and the mechanism of the pyridoxal phosphate dependent reactions of the bacterial tryptophan synthase alpha 2 beta 2 complex by use of substrate analogues and of reaction intermediate analogues. Fluorine-19 nuclear magnetic resonance studies
Warintra Pitsawong et al.
eLife, 7 (2018-06-15)
Protein kinases are major drug targets, but the development of highly-selective inhibitors has been challenging due to the similarity of their active sites. The observation of distinct structural states of the fully-conserved Asp-Phe-Gly (DFG) loop has put the concept of
Kenji Hamase et al.
Journal of chromatography. A, 1106(1-2), 159-164 (2006-01-31)
A sensitive assay for D-amino-acid oxidase (DAO) activity in mammalian tissues has been established. D-Tryptophan (D-Trp) analogs were tested as substrates for DAO, and 5-fluoro-D-tryptophan (D-FTP) was found to be the best substrate. By the enzymatic reaction, D-FTP was converted

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