N-α-Dansyl-L-alanine cyclohexylammonium salt
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N-α-Dansyl-L-alanine cyclohexylammonium salt

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Category
L-Amino Acids
Catalog number
BAT-006938
CAS number
53332-27-7
Molecular Formula
C21H31N3O4S
Molecular Weight
421.55
N-α-Dansyl-L-alanine cyclohexylammonium salt
IUPAC Name
cyclohexanamine;(2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]propanoic acid
Synonyms
Dns-Ala-OH CHA; Dansyl-Ala-OH CHA; N-α-{[5-(Demethylamino)-1-naphthalenyl]sulfonyl}-L-alanine cyclohexylammonium salt
Appearance
Light Yellow to Light Green Powder
Purity
35021-10-4 (Free Acid)
Boiling Point
526°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
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
Canonical SMILES
CC(C(=O)O)NS(=O)(=O)C1=CC=CC2=C1C=CC=C2N(C)C.C1CCC(CC1)N

N-α-Dansyl-L-alanine cyclohexylammonium salt, a fluorescent amino acid derivative widely utilized in biochemical and analytical realms, boasts diverse applications. Here are the key applications presented with a high degree of perplexity and burstiness:

Protein Labeling: Harnessing the capabilities of N-α-Dansyl-L-alanine cyclohexylammonium salt, researchers adorn proteins with a fluorescent tag, facilitating the exploration of protein localization, interactions, and functions. The fluorescence emanating from the dansyl group serves as a sensitive tool for detecting and quantifying labeled proteins across various assays. This application finds particular utility in fluorescence microscopy and flow cytometry, offering a nuanced lens into the intricate world of proteins.

Enzyme Assays: In enzyme assays, this compound takes center stage, enabling the real-time monitoring of enzyme activity and kinetics. By embedding the fluorescent tag into enzyme substrates, researchers track changes in fluorescence as the substrate undergoes conversion to product. This methodology empowers high-throughput screening of enzyme inhibitors and activators, pushing the boundaries of enzymology research.

Peptide Synthesis: Embraced in the creation of fluorescently labeled peptides, N-α-Dansyl-L-alanine cyclohexylammonium salt fuels binding studies and assays involving peptides. These labeled peptides serve as invaluable tools in investigating receptor-ligand interactions, protease activity, and beyond. Such applications play a pivotal role in sculpting the landscape of peptide-based therapeutics and diagnostics, unveiling new vistas in peptide research.

Cellular Imaging: A stalwart in the realm of cellular imaging, N-α-Dansyl-L-alanine cyclohexylammonium salt steps forward to stain and illuminate cellular structures. Its fluorescent properties render it ideal for incorporation in diverse imaging techniques, such as confocal microscopy. By leveraging its prowess, researchers peer deep into the inner workings of cellular components and processes, gaining insights with unprecedented specificity and sensitivity.

1. Synthesis of α-D-Ribose 1-Phosphate and 2-Deoxy-α-D-Ribose 1-Phosphate Via Enzymatic Phosphorolysis of 7-Methylguanosine and 7-Methyldeoxyguanosine
Irina V Varizhuk, Vladimir E Oslovsky, Pavel N Solyev, Mikhail S Drenichev, Sergey N Mikhailov Curr Protoc. 2022 Jan;2(1):e347. doi: 10.1002/cpz1.347.
A simple and efficient method for the preparation of α-D-ribose 1-phosphate and 2-deoxy-α-D-ribose 1-phosphate, key intermediates in nucleoside metabolism and important starting compounds for the enzymatic synthesis of various modified nucleosides, has been proposed. It consists in near-irreversible enzymatic phosphorolysis of readily prepared hydroiodide salts of 7-methylguanosine and 7-methyl-2'-deoxyguanosine, respectively, in the presence of purine nucleoside phosphorylase. α-D-Ribose 1-phosphate and 2-deoxy-α-D-ribose 1-phosphate are obtained in near quantitative yields (by HPLC analysis) and 74%-94% yields after their isolation and purification. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Preparation of α-D-ribose 1-phosphate barium salt (4a) Alternate Protocol 1: Preparation of 2-deoxy-α-D-ribose 1-phosphate barium salt (4b) Basic Protocol 2: Preparation of α-D-ribose 1-phosphate bis(cyclohexylammonium) salt (5a) Alternate Protocol 2: Preparation of 2-deoxy-α-D-ribose 1-phosphate bis(cyclohexylammonium) salt (5b).
2. Bis(cyclohexylammonium) 2,2'-disulfanediyldibenzoate
Xinting Wei, Jing Li, Handong Yin Acta Crystallogr Sect E Struct Rep Online. 2011 Jan 12;67(Pt 2):o319. doi: 10.1107/S1600536810054012.
In the title molecular salt, 2C(6)H(14)N(+)·C(14)H(8)O(4)S(2) (2-), the complete dianion is generated by crystallographic twofold symmetry and a twisted conformation is found [the C-S-S-C torsion angle is 87.13 (2)° and the dihedral angle between the rings is 83.4 (2)°]. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the cations and anions.
3. Bis(cyclo-hexyl-ammonium) tetra-bromido-cuprate(II)
Meng Ting Han Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):m448. doi: 10.1107/S1600536812011117. Epub 2012 Mar 21.
The structure of the title salt, (C(6)H(14)N)(2)[CuBr(4)], is built up from cyclo-hexyl-ammonium cations and tetra-bromidocuprate anions, the latter being located on an inversion center. In the crystal, anions and cations are inter-connected by N-H⋯Br hydrogen bonds, forming ribbons parallel to [0-11].
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