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907340

Sigma-Aldrich

H-L-Photo-Phe-OH

≥98%

Synonym(s):

(S)-2-Amino-3-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)propanoic acid, 4-(Trifluoromethyldiazirin)-L-phenylalanine, Diazirine amino acid, H-Tdf-OH, Photo-Phe, Photo-crosslinking amino acid, Photoprobe building block

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About This Item

Empirical Formula (Hill Notation):
C11H10F3N3O2
CAS Number:
92367-16-3
Molecular Weight:
273.21
MDL number:
MFCD30187606
UNSPSC Code:
12352101

Assay

≥98%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

availability

available only in USA

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

FC(F)(F)C2(N=N2)c1ccc(cc1)CC(N)C(=O)O

InChI

1S/C11H10F3N3O2/c12-11(13,14)10(16-17-10)7-3-1-6(2-4-7)5-8(15)9(18)19/h1-4,8H,5,15H2,(H,18,19)

InChI key

HRGXDARRSCSGOG-UHFFFAOYSA-N

Related Categories

Application

H-L-Photo-Phe-OH is a diazirine-containing phenylalanine amino acid and multifunctional
photo-crosslinker. Its incorporation into peptides or small-molecule probes and tools allows for photoaffinity labeling of cellular targets and protein-protein interactions upon UV light (∼360 nm) irradiation to form a covalent bond. This and other multifunctional probe building blocks will continue to accelerate drug discovery research for probing cellular mechanisms, target ID/validation, and understanding traditionally undruggable targets. An Fmoc-protected version is also available as 907294.

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

Other Notes

Genetic Incorporation of a Photo-Crosslinkable Amino Acid Reveals Novel Protein Complexes with GRB2 in Mammalian Cells

Trifluoromethyldiazirine: an effective photo-induced cross-linking probe for exploring amyloid formation

A genetically encoded diazirine photo-crosslinker in Escherichia coli

Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis

Photo-affinity labeling (PAL) in chemical proteomics: a handy tool to investigate protein-protein interactions (PPIs)

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H242

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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A genetically encoded diazirine photocrosslinker in Escherichia coli.
Eric M Tippmann et al.
Chembiochem : a European journal of chemical biology, 8(18), 2210-2214 (2007-11-15)
Lei Wang et al.
Organic letters, 17(3), 616-619 (2015-01-15)
Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2(-) is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
Lei Wang et al.
Molecules (Basel, Switzerland), 18(7), 8393-8401 (2013-07-19)
Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores--aryl azide, benzophenone and trifluoromethyldiazirine--are utilized in analysis. Photophore-bearing L-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the
Lei Wang et al.
Bioscience, biotechnology, and biochemistry, 78(7), 1129-1134 (2014-09-18)
In this paper we report here a hydrogen/deuterium exchange (H/D exchange) of cross-linkable α-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o-catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange
R Falchetto et al.
The Journal of biological chemistry, 266(5), 2930-2936 (1991-02-15)
A synthetic, 28-residue peptide derived from the calmodulin-binding sequence of the plasma membrane Ca2+ pump (C28W) inhibits the ATPase activity of a calpain-produced, truncated fragment of the enzyme. The fragment, which has lost the calmodulin-binding domain, has a molecular mass
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