Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin

Yoshihiro Abe; Tomoko Shoji; Mamiko Matsubara; Midori Yoshida; Setsuro Sugata; Kazunori Iwata; Hiroshi Suzuki

doi:10.1002/1520-636x(2000)12:7<565::aid-chir3>3.0.co;2-%23

Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin

Yoshihiro Abe, Tomoko Shoji, Mamiko Matsubara, Midori Yoshida, Setsuro Sugata, Kazunori Iwata, Hiroshi Suzuki

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C₁-C₄) 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 (C₁), amino butyric acid (C₂), norvaline (C₃), and norleucine (C₄) 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. (C) 2000 Wiley-Liss, Inc.

Original language	English
Pages (from-to)	565-567
Number of pages	3
Journal	Chirality
Volume	12
Issue number	7
DOIs	https://doi.org/10.1002/1520-636x(2000)12:7<565::aid-chir3>3.0.co;2-%23
Publication status	Published - 2000 Jan 1

Keywords

Bovine serum albumin
Carbazole-carbonyl amino acids
Chiral discrimination
Enantioseparation
HPLC

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/1520-636x(2000)12:7<565::aid-chir3>3.0.co;2-%23

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title = "Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin",

abstract = "Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C1-C4) 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 (C1), amino butyric acid (C2), norvaline (C3), and norleucine (C4) 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. (C) 2000 Wiley-Liss, Inc.",

keywords = "Bovine serum albumin, Carbazole-carbonyl amino acids, Chiral discrimination, Enantioseparation, HPLC",

author = "Yoshihiro Abe and Tomoko Shoji and Mamiko Matsubara and Midori Yoshida and Setsuro Sugata and Kazunori Iwata and Hiroshi Suzuki",

year = "2000",

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doi = "10.1002/1520-636x(2000)12:7<565::aid-chir3>3.0.co;2-%23",

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journal = "Chirality",

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T1 - Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin

AU - Abe, Yoshihiro

AU - Shoji, Tomoko

AU - Matsubara, Mamiko

AU - Yoshida, Midori

AU - Sugata, Setsuro

AU - Iwata, Kazunori

AU - Suzuki, Hiroshi

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C1-C4) 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 (C1), amino butyric acid (C2), norvaline (C3), and norleucine (C4) 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. (C) 2000 Wiley-Liss, Inc.

AB - Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C1-C4) 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 (C1), amino butyric acid (C2), norvaline (C3), and norleucine (C4) 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. (C) 2000 Wiley-Liss, Inc.

KW - Bovine serum albumin

KW - Carbazole-carbonyl amino acids

KW - Chiral discrimination

KW - Enantioseparation

KW - HPLC

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AN - SCOPUS:0034095706

SN - 0899-0042

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JF - Chirality

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ER -

Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin

Abstract

Keywords

ASJC Scopus subject areas

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