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914584

Sigma-Aldrich

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
MDL number:
MFCD30187602
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

storage temp.

2-8°C

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(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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