Chiral discrimination of N-carbazole-carbonyl derivatives of alpha-amino acids with a short linear alkyl side chain by bovine serum albumin.
Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C(1)-C(4)) by bovine serum albumin (BSA) was investigated by competitive replacement experiments using dansyl-L-proline and dansyl-D-norvaline as fluorescent probes. It was found that the CC derivatives of the D-forms of alanine (C(1)), amino butyric acid (C(2)), norvaline (C(3)), and norleucine (C(4)) bound to the dansyl-L-proline site much more strongly than their L-forms, whereas the interactions between both enantiomers of these amino acids with dansyl-D-norvaline site were slight.
Abe
Y
Y
Kyoritsu College of Pharmacy, Tokyo, Japan. abe-ys@kyoritsu-ph.ac.jp
Shoji
T
T
Matsubara
M
M
Yoshida
M
M
Sugata
S
S
Iwata
K
K
Suzuki
H
H
D000409:Alanine / Q000737:chemistry; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D001665:Binding Sites; D002227:Carbazoles / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003619:Dansyl Compounds / Q000737:chemistry; D011392:Proline / Q000737:chemistry; D011485:Protein Binding; D012710:Serum Albumin, Bovine / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014633:Valine / Q000737:chemistry
D000596:Amino Acids; D002227:Carbazoles; D003619:Dansyl Compounds; D012710:Serum Albumin, Bovine; D011392:Proline; D014633:Valine; D000409:Alanine