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914584

Sigma-Aldrich

Phenylalanine-4′-azobenzene HCl

≥95%

Synonym(e):

(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

Empirische Formel (Hill-System):
C15H16ClN3O2
CAS-Nummer:
Molekulargewicht:
305.76
MDL-Nummer:
UNSPSC-Code:
12352209
NACRES:
NA.22

Qualitätsniveau

Assay

≥95%

Form

powder

Lagertemp.

2-8°C

SMILES String

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

InChIKey

LRSKKAMIJGFIDZ-GUFYRWSKSA-N

Anwendung

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)

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Preisangaben

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Koji Nakayama et al.
Chemical communications (Cambridge, England), (21), 2386-2387 (2004-10-30)
Endonuclease BamHI mutants having an azophenylalanine residue in the dimer interface (azoAla-BamHI) were synthesized; while the activity was almost suppressed using trans-azoAla-BamHI, the cis-isomer generated with photoirradiation recovered its intrinsic activity.
Hiroshi Murakami et al.
Chemistry & biology, 10(7), 655-662 (2003-08-02)
Aminoacyl-tRNA synthetase (ARS) ribozymes have potential to develop a novel genetic coding system. Although we have previously isolated such a ribozyme that recognizes aromatic amino acids, it could not be used as a versatile catalyst due to its limited ability
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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