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  • Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen.

Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen.

Chirality (2001-12-19)
Akihiko Ouchi, Giorgia Zandomeneghi, Maurizio Zandomeneghi
ABSTRACT

The reactivity of organic molecules can be modified upon complexation with proteins: these changes can be different and more significant when the substrate is in an electronically excited state. Here we review UV, CD, and fluorescence spectroscopy studies on the photochemistry and on the chemistry of atropisomeric binaphthols and of ketoprofen, complexed to serum albumins. The chemical and photochemical properties of the organic substrates, complexed to the albumins or free in common solvents, are different. The role of the protein complexation is also evidenced in photoresolution processes of racemate-protein complexes. Catalytic effects due to serum albumins are also reported. In particular, the Arrhenius parameters for the rate of thermal isomerization of a metastable photoproduct of binaphthol in common solvents are compared with those of the bovine serum albumin catalyzed isomerization.

MATERIALS
Product Number
Brand
Product Description

Supelco
Ketoprofen, VETRANAL®, analytical standard
Sigma-Aldrich
Ketoprofen, ≥98% (TLC)
Sigma-Aldrich
Ketoprofen, meets USP testing specifications
Ketoprofen, European Pharmacopoeia (EP) Reference Standard
USP
Ketoprofen, United States Pharmacopeia (USP) Reference Standard
Supelco
Ketoprofen, Pharmaceutical Secondary Standard; Certified Reference Material