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D0125

Sigma-Aldrich

Dansyl-L-alanine cyclohexylammonium salt

≥98% (TLC), suitable for protein expression

Synonym(e):

N-[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]- L-alanine cyclohexylammonium salt

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About This Item

Empirische Formel (Hill-System):
C15H18N2O4S · C6H13N
CAS-Nummer:
53332-27-7
Molekulargewicht:
421.55
EG-Nummer:
258-478-3
MDL-Nummer:
MFCD00038927
UNSPSC-Code:
12352209
PubChem Substanz-ID:
329798584
NACRES:
NA.26

product name

Dansyl-L-alanine cyclohexylammonium salt, fluorescent amino acid

Assay

≥98% (TLC)

Form

powder

Methode(n)

protein expression: suitable

Lagertemp.

−20°C

SMILES String

NC1CCCCC1.C[C@H](NS(=O)(=O)c2cccc3c(cccc23)N(C)C)C(O)=O

InChI

1S/C15H18N2O4S.C6H13N/c1-10(15(18)19)16-22(20,21)14-9-5-6-11-12(14)7-4-8-13(11)17(2)3;7-6-4-2-1-3-5-6/h4-10,16H,1-3H3,(H,18,19);6H,1-5,7H2/t10-;/m0./s1

InChIKey

CZUBQNQWSOLSJH-PPHPATTJSA-N

Anwendung

Alanine conjugated to the fluorophore 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl). The unnatural amino acid has been incorporated into expressed proteins by use of a mutated aminoacyl-tRNA synthetase specific for dansylalanine.

Biochem./physiol. Wirkung

Dansyl-L-alanine contains an N-terminal fluorophore (dansyl) making it useful as a fluorescent marker/probe. Dansylalanine can be incorporated into proteins by newly developing techniques that expand the genetic code.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Hyun Soo Lee et al.
Journal of the American Chemical Society, 131(36), 12921-12923 (2009-08-26)
Here, we report that the fluorescent amino acid, 3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid (Anap), can be genetically incorporated into proteins in yeast with excellent selectivity and efficiency by means of an orthogonal tRNA/aminoacyl-tRNA synthetase pair. This small, environmentally sensitive fluorophore was site-specifically incorporated
Esterification of an unnatural amino acid structurally deviating from canonical amino acids promotes its uptake and incorporation into proteins in mammalian cells.
Jeffrey K Takimoto et al.
Chembiochem : a European journal of chemical biology, 11(16), 2268-2272 (2010-09-28)
Wenyuan Wang et al.
Nature neuroscience, 10(8), 1063-1072 (2007-07-03)
Proteins participate in various biological processes and can be harnessed to probe and control biological events selectively and reproducibly, but the genetic code limits the building block to 20 common amino acids for protein manipulation in living cells. The genetic
Daniel Summerer et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(26), 9785-9789 (2006-06-21)
The ability to introduce fluorophores selectively into proteins provides a powerful tool to study protein structure, dynamics, localization, and biomolecular interactions both in vitro and in vivo. Here, we report a strategy for the selective and efficient biosynthetic incorporation of
A genetically encoded fluorescent amino acid.
Summerer, D., et al.
Proceedings of the National Academy of Sciences of the USA, 108, 9785-9789 (2006)
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