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915793

Sigma-Aldrich

Methyl-o-nitropiperonyllysine

≥95%

Sinónimos:

N6-((1-(6-Nitrobenzo[d][1,3]dioxol-5-yl)ethoxy)carbonyl)-L-lysine, Light-triggered decaging Lys, Photo-controlled amino acid, Photocaged amino acid, Photocleavable lysine derivative, mNPK

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About This Item

Fórmula empírica (notación de Hill):
C16H21N3O8
Número de CAS:
1221189-11-2
Peso molecular:
383.35
Número MDL:
MFCD30474478
Código UNSPSC:
12352209
NACRES:
NA.22

Nivel de calidad

100

Ensayo

≥95%

Formulario

powder

temp. de almacenamiento

−20°C

cadena SMILES

[N+](=O)([O-])c1cc2c(cc1C(OC(=O)NCCCC[C@H](N)C(=O)O)C)OCO2

InChI

1S/C16H21N3O8/c1-9(27-16(22)18-5-3-2-4-11(17)15(20)21)10-6-13-14(26-8-25-13)7-12(10)19(23)24/h6-7,9,11H,2-5,8,17H2,1H3,(H,18,22)(H,20,21)/t9?,11-/m0/s1

Clave InChI

ZXXFKVZFDGUTQW-UMJHXOGRSA-N

Aplicación

Methyl-o-nitropiperonyllysine (mNPK) trifluoroacetic acid is a photo-responsive unnatural amino acid (UAA) for spatiotemporal control of biological molecules or processes as reported by Kneuttinger et al. Irradiation with UV light decages the Lys amino acid, freeing the residue or protein for biological activity. Tools such as mNPK will find wide utility in light regulation of activity, allostery, and enzyme pathways.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Otras notas

Light Regulation of Enzyme Allostery through Photoresponsive Unnatural Amino Acids

Precise Photoremovable Perturbation of a Virus-Host Interaction

Genetic code expansion in the mouse brain

Genetically encoded optical activation of DNA recombination in human cells

Bioorthogonal Chemical Activation of Kinases in Living Systems

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Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKCW3455
MKCM9525

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Arnaud Gautier et al.
Journal of the American Chemical Society, 133(7), 2124-2127 (2011-01-29)
We report a general strategy for creating protein kinases in mammalian cells that are poised for very rapid activation by light. By photoactivating a caged version of MEK1, we demonstrate the specific, rapid, and receptor independent activation of an artificial
James Hemphill et al.
Journal of the American Chemical Society, 135(36), 13433-13439 (2013-08-13)
Photocaging provides a method to spatially and temporally control biological function and gene expression with high resolution. Proteins can be photochemically controlled through the site-specific installation of caging groups on amino acid side chains that are essential for protein function.
Arnaud Gautier et al.
Journal of the American Chemical Society, 132(12), 4086-4088 (2010-03-12)
Precise photochemical control of protein function can be achieved through the site-specific introduction of caging groups. Chemical and enzymatic methods, including in vitro translation and chemical ligation, have been used to photocage proteins in vitro. These methods have been extended
Olivia S Walker et al.
Journal of the American Chemical Society, 138(3), 718-721 (2016-01-14)
Isocitrate dehydrogenase is mutated at a key active site arginine residue (Arg172 in IDH2) in many cancers, leading to the synthesis of the oncometabolite (R)-2-hydroxyglutarate (2HG). To investigate the early events following acquisition of this mutation in mammalian cells we
Sarah B Erickson et al.
Angewandte Chemie (International ed. in English), 56(15), 4234-4237 (2017-03-16)
Viruses utilize distinct binding interactions with a variety of host factors to gain entry into host cells. A chemical strategy is described to precisely perturb a specific molecular interaction between adeno-associated virus and its host cell, which can be rapidly
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