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Merck

47568

Sigma-Aldrich

5-Fluoro-L-tryptophan

≥98.0% (HPLC)

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About This Item

经验公式(希尔记法):
C11H11FN2O2
CAS号:
分子量:
222.22
Beilstein:
5052680
MDL號碼:
分類程式碼代碼:
12352202
eCl@ss:
32160406
PubChem物質ID:
NACRES:
NA.77

化驗

≥98.0% (HPLC)

形狀

powder

光學純度

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

270-280 °C

儲存溫度

2-8°C

SMILES 字串

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 密鑰

INPQIVHQSQUEAJ-VIFPVBQESA-N

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應用

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)


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分析证书(COA)

Lot/Batch Number

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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.
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
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
S Rozovsky et al.
Journal of molecular biology, 310(1), 271-280 (2001-06-23)
Product release is partially rate determining in the isomerization reaction catalyzed by Triosephosphate Isomerase, the conversion of dihydroxyacetone phosphate to D-glyceraldehyde 3-phosphate, probably because an active-site loop movement is necessary to free the product from confinement in the active-site. The

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