4-Benzoyl-L-phenylalanin - 4-Benzoyl-L-phenylalanin

Structural formula
4-Benzoyl-L-phenylalanin
General
Name 4-Benzoyl-L-phenylalanin
other names
  • p-Benzoyl-phenylalanin
  • (S)-4-Benzoyl-phenylalanin
  • L -Bpa-OH
  • H-L-Phe(4-Bz)-OH
  • p-BzF
Sum formula C 16 H 15 NO 3
Brief description

colorless powder [1]

External identifiers / databases
CAS number 104504-45-2
PubChem 7020128
ChemSpider 5383084
DrugBank DB08371
Wikidata Q27097586
characteristics
Molar mass 269.3 g · mol −1
Physical state

fest[2]

safety instructions
GHS hazard labeling [2]
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases [2]
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Benzoyl- L- phenylalanine is a chemical compound from the group of non-proteinogenic amino acids .

characteristics

4-Benzoyl- L- phenylalanine is used in biochemistry for crosslinking and for the photoaffinity labeling of proteins . [3] [4] [5] It is incorporated into proteins in the course of a peptide synthesis instead of tyrosine . Subsequent exposure to UV light triggers the radical crosslinking reaction. [6]

Individual evidence

  1. J&K Scientific: 4-Benzoyl-L-phenylalanine, 95% , accessed October 1, 2018.
  2. a b c Data sheet 4-Benzoyl-L-phenylalanine, 95% from AlfaAesar, accessed on February 20, 2018 ( PDF )(JavaScript required) .
  3. J. R. Starkey, S. Uthayakumar, D. L. Berglund: Cell surface and substrate distribution of the 67-kDa laminin-binding protein determined by using a ligand photoaffinity probe. In: Cytometry. Band 35, Nummer 1, Januar 1999, S. 37–47, PMID 10554179.
  4. L. K. Henry, S. Khare, C. Son, V. V. Babu, F. Naider, J. M. Becker: Identification of a contact region between the tridecapeptide alpha-factor mating pheromone of Saccharomyces cerevisiae and its G protein-coupled receptor by photoaffinity labeling. In: Biochemistry. Band 41, Nummer 19, Mai 2002, S. 6128–6139, PMID 11994008.
  5. F. L. Yeh, L. Tung, T. H. Chang: Detection of Protein-Protein Interaction Within an RNA-Protein Complex Via Unnatural-Amino-Acid-Mediated Photochemical Crosslinking. In: Methods in molecular biology. Band 1421, 2016, S. 175–189, doi:10.1007/978-1-4939-3591-8_15, PMID 26965266.
  6. D. Volke, A. Krizsan, N. Berthold, D. Knappe, R. Hoffmann: Identification of Api88 Binding Partners in Escherichia coli Using a Photoaffinity-Cross-Link Strategy and Label-Free Quantification. In: Journal of proteome research. Band 14, Nummer 8, August 2015, S. 3274–3283, doi:10.1021/acs.jproteome.5b00283, PMID 26196380.