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D0125

Sigma-Aldrich

Dansyl-L-alanine cyclohexylammonium salt

fluorescent amino acid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H18N2O4S · C6H13N
CAS Number:
53332-27-7
Molecular Weight:
421.55
EC Number:
258-478-3
MDL number:
MFCD00038927
UNSPSC Code:
12352209
PubChem Substance ID:
329798584
NACRES:
NA.26

Quality Level

200

assay

≥98% (TLC)

form

powder

technique(s)

protein expression: suitable

storage temp.

−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

InChI key

CZUBQNQWSOLSJH-PPHPATTJSA-N

Related Categories

Application

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 Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (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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