Chiral recognition of dipeptide methyl esters by an anionic β-cyclodextrin

Chirality

Volumn 13, Issue 8, 2001, Pages 474-482

  Kano, Koji ^a   Hasegawa, Hideki ^a   Miyamura, Muneki ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

1H NMR; Anionic cyclodextrin; Chiral recognition; Coulomb interactions; Dipeptide methyl esters; Mechanism

Indexed keywords

ALANINE DERIVATIVE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; BETA CYCLODEXTRIN; DIPEPTIDE; LEUCINE; TRYPTOPHAN DERIVATIVE;

AMINO TERMINAL SEQUENCE; BINDING AFFINITY; CHIRALITY; COMPLEX FORMATION; CONFERENCE PAPER; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIONS; BETA-CYCLODEXTRINS; CYCLODEXTRINS; DIPEPTIDES; ESTERS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR;

EID: 0034897924     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.1064     Document Type: Conference Paper

References (11)

1. Bender ML, Komiyama M. Cyclodextrin chemistry. New York: Springer-Verlag; 1978.
2. Cramer F, Dietsche W. Spaltung von Racemation mit Cyclodextrinen. Chem Ber 1959;92:378-385.
3. (a) Kano K. Mechanisms for chiral recognition by cyclodextrins. J Phys Org Chem 1997;10:286-291.
4. (b) Rekharsky, M, Inoue, Y. Chiral recognition thermodynamics of β-cyclodextrin: The thermodynamic origin of enantioselectivity and the enthalpy-entropy compensation effect. J Am Chem Soc 2000;122:4418-4435.
5. Cooper A, MacNicol DD. Chiral host-guest complexes: interaction of α-cyclodextrin with optically active benzene derivatives. J Chem Soc, Perkin Trans 2 1978:760-763.
6. 13C NMR studies of formation and molecular dynamics of methylated cyclodextrin inclusion complexes with phenylalanine. Bull Chem Soc Jpn 1987;60:2539-2545.
7. Lipkowitz KB, Raghothama S, Yang J. Enantioselective binding of tryptophan by α-cyclodextrin. J Am Chem Soc 1992;114:1554-1562.
8. Many studies on chiral separation of α-amino acids and their derivatives by capillary electrophoresis, gas chromatography, and HPLC have been carried out using CDs as chiral selectors. For recent ex-amples, see: (a) Zhang M, El Rassi Z. Enantiomeric separation by capillary electrochromatography. II. Chiral separation of dansyl amino acids and phenoxy acid herbicides on sulfonated silica having surface-bound hydroxypropyl-β-cyclodextrin. Electrophoresis 2000:21:3135-3140.
9. (b) Miura M, Terashima Y, Funazo K, Tanaka M. Chiral separation of naphthoylamino acids by capillary zone electrophoresis with selectively methylated cyclodextrin derivatives. Anal Sci 1999:15:299-302.
10. Easton CJ, Lincoln SF. Modified cyclodextrins. London: Imperial College Press; 1999. p 71-100.
11. Acarboxy-β-cyclodextrins. J Am Chem Soc 1986;108:4514-4518.