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Merck
CN

914584

Phenylalanine-4′-azobenzene HCl

≥95%

Synonym(s):

(2S)-2-Amino-3-[4-(2-phenyldiazen-1-yl)phenyl]propanoic acid hydrochloride, (E)-2-Amino-3-(4-(phenyldiazenyl)phenyl)propanoic acid HCl, 4-(2-Phenyldiazenyl)-L-phenylalanine hydrochloride, 4-(Phenylazo)-L-phenylalanine, AzoF, Photoswitchable phenylalanine amino acid, Reversible photo-controllable unnatural amino acid

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About This Item

Empirical Formula (Hill Notation):
C15H16ClN3O2
CAS Number:
2137036-84-9
Molecular Weight:
305.76
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD30187602

Key Documents

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Product Name

Phenylalanine-4′-azobenzene HCl, ≥95%

SMILES string

Cl.N[C@@H](Cc1ccc(cc1)\N=N\c2ccccc2)C(=O)O

InChI key

LRSKKAMIJGFIDZ-GUFYRWSKSA-N

assay

≥95%

form

powder

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Phenylalanine-4′-azobenzene HCl (AzoF) is a phenylalanine derivative with an azo bond that isomerizes upon UV irradiation from its E isomer to its Z isomer and reverts back at light above 400 nm. When incorporated into proteins or chemical probes, this reversibility is utilized as a photoswitch with spatial and temporal regulation within biological systems.

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

Other Notes

Light Regulation of Enzyme Allostery through Photo-responsive Unnatural Amino Acids

Photochemical control of enzymes using photoresponsive compounds on the basis of the interaction mechanism

Photochemical regulation of the activity of an endonuclease BamHI using an azobenzene moiety incorporated site-selectively into the dimer interface

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM4743

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Andrea C Kneuttinger et al.
Cell chemical biology, 26(11), 1501-1514 (2019-09-10)
Imidazole glycerol phosphate synthase (ImGPS) is an allosteric bienzyme complex in which substrate binding to the synthase subunit HisF stimulates the glutaminase subunit HisH. To control this stimulation with light, we have incorporated the photo-responsive unnatural amino acids phenylalanine-4'-azobenzene (AzoF)

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