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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

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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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.
G Baldini et al.
Biochemistry, 27(20), 7951-7959 (1988-10-04)
The Boc-protected derivative of a photoactivatable, carbene-generating analogue of phenylalanine, L-4'-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenylalanine [(Tmd)Phe], was used to acylate 5'-O-phosphorylcytidylyl(3'-5')adenosine (pCpA). A diacyl species was isolated which upon successive treatments with trifluoroacetic acid and 0.01 M HCl yielded a 1:1 mixture of 2'(3')-O-(Tmd)phenylalanyl-pCpA
Nobumasa Hino et al.
Journal of molecular biology, 406(2), 343-353 (2010-12-28)
Cell signaling pathways are essentially organized through the distribution of various types of binding domains in signaling proteins, with each domain binding to specific target molecules. Although identification of these targets is crucial for mapping the pathways, affinity-based or copurification
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.
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
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