Enantioselective binding sites on bovine serum albumin to dansyl amino acids.
The enantioselective binding sites on bovine serum albumin were examined by HPLC using 19 racemic 5-N, N-dimethylamino-1-naphthalenesulfonyl derivatives of alpha-amino acids (dansyl amino acids) as chiral probes. On a bovine serum albumin bonded chiral stationary phase, seven L-forms eluted faster than their D-forms, while ten D-forms eluted before their L-forms. It was speculated that either two classes or two different binding sites exist on bovine serum albumin which can be distinguished by N-dansyl-L-proline and N-dansyl-D-norvaline. This was confirmed by fluorometric experiments where non-fluorescent 1-naphthalenesulfonyl derivatives were synthesized and competitive adsorption experiments were performed.
Abe
Y
Y
Kyoritsu College of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
Fukui
S
S
Koshiji
Y
Y
Kobayashi
M
M
Shoji
T
T
Sugata
S
S
Nishizawa
H
H
Suzuki
H
H
Iwata
K
K
D000596:Amino Acids / Q000737:chemistry*; D001665:Binding Sites; D001667:Binding, Competitive; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003619:Dansyl Compounds / Q000737:chemistry*; D009282:Naphthalenesulfonates / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry; D014859:Warfarin / Q000737:chemistry
D000596:Amino Acids; D003619:Dansyl Compounds; D009282:Naphthalenesulfonates; C086697:dansylproline; D012710:Serum Albumin, Bovine; D014859:Warfarin; D011392:Proline; C005313:norvaline; D014633:Valine