A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, alpha-amino acid.
The novel alpha-amino acid BpAib, a partially conformationally restricted analogue of the currently extensively used 3-(4-benzoylphenyl)alanine (Bpa) photoaffinity label, was synthesized, optically resolved, fully characterized, and appropriately derivatized. An intermolecular photocrosslinking experiment highlighted its regioselective reactivity towards the S-methyl side-chain group of a Met-based dipeptide, which is closely comparable to that of Bpa.
Wright
Karen
K
ILV, UMR CNRS 8180, University of Versailles, 78035 Versailles, France. wright@chimie.uvsq.fr
Moretto
Alessandro
A
Crisma
Marco
M
Wakselman
Michel
M
Mazaleyrat
Jean-Paul
JP
Formaggio
Fernando
F
Toniolo
Claudio
C
D000409:Alanine / Q000138:chemical synthesis* / Q000737:chemistry*; D001577:Benzophenones / Q000737:chemistry*; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry*; D055668:Photochemical Processes; D013057:Spectrum Analysis
D001577:Benzophenones; D019920:Photoaffinity Labels; C047723:benzophenone; D000409:Alanine