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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)565-567
Number of pages3
JournalChirality
Volume12
Issue number7
DOIs
Publication statusPublished - 2000

Fingerprint

Bovine Serum Albumin
Amino acids
Derivatives
Amino Acids
Proline
Norleucine
L Forms
Butyric acid
Butyric Acid
Enantiomers
Fluorescent Dyes
Alanine
carbazole
norvaline
Experiments
dansylproline

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin. / Abe, Yoshihiro; Shoji, Tomoko; Matsubara, Mamiko; Yoshida, Midori; Sugata, Setsuro; Iwata, Kazunori; Suzuki, Hiroshi.

In: Chirality, Vol. 12, No. 7, 2000, p. 565-567.

Research output: Contribution to journalArticle

Abe, Yoshihiro ; Shoji, Tomoko ; Matsubara, Mamiko ; Yoshida, Midori ; Sugata, Setsuro ; Iwata, Kazunori ; Suzuki, Hiroshi. / Chiral discrimination of N-carbazole-carbonyl derivatives of α-amino acids with a short linear alkyl side chain by bovine serum albumin. In: Chirality. 2000 ; Vol. 12, No. 7. pp. 565-567.
@article{716ace3ec09645469ac20aa8c6f89595,
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",
doi = "10.1002/1520-636X(2000)12:7<565::AID-CHIR3>3.0.CO;2-#",
language = "English",
volume = "12",
pages = "565--567",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "7",

}

TY - JOUR

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

Y1 - 2000

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

UR - http://www.scopus.com/inward/record.url?scp=0034095706&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034095706&partnerID=8YFLogxK

U2 - 10.1002/1520-636X(2000)12:7<565::AID-CHIR3>3.0.CO;2-#

DO - 10.1002/1520-636X(2000)12:7<565::AID-CHIR3>3.0.CO;2-#

M3 - Article

VL - 12

SP - 565

EP - 567

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 7

ER -