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CHIRAL RECOGNITION BY MULTI POINT INTERACTION STUDIED BY MICROCALORIMETRY AND HIGH RESOLUTIONALNMR SPECTROMETRY

Research Project

Project/Area Number 17550127
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionNagoya Institute of Technology

Principal Investigator

YAMAMURA Hastuo  Nagoya Institute of Technology, GRADUATE SCHOOL OF ENGINEERING, ASSOCIATE PROFESSOR (80220440)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2006: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2005: ¥3,100,000 (Direct Cost: ¥3,100,000)
Keywordstitration calorimetry / chiral recoenition / cyclodextrin / 高分解能NMR
Research Abstract

Complex stability constant, standard free energy (△G^O), reaction enthalpy (△H^O), and entropy change (T△S^O) for 1:1 inclusion complexation of the chiral amino acids Z-D/L-Trp (Z = benzyloxycarbonyl), Ac-D/L-Trp (Z = acetyl) with β-cyclodextrins (β-CDs) modified with D/L-Trp moiety and D/L-naphtylalaine moiety (D/L-Trp-β-CD and D/L-Naph-β-CDs) were determined by isothermal titration microcalorimetry. Interaction of Z-D/L-Trp with D/L-Trp-β-CD revealed no chiral discrimination. Affinities were smaller than that observed with native β-CD, however enthalpies were more negative in the case of D/L-Trp-β-CD. Affinities of Ac-D/L-Trp toward D/L-Trp-β-CD were higher than that toward native β-CD in 2-5 times. Binding properties of D-Trp-β-CD were quite different from the properties of L-Trp-β-CD, although both hosts exhibited no enantioselective abilities. Similarly to D/L-Trp-β-CD, D/L-Naph-β-CD also exhibited very low ability to discriminate between enantiomers of Ac-Trp. Upon interaction of two opposite enantiomers of Ac-Trp with L-Naph-β-CD quite different reaction enthalpies were observed. Nevertheless, stability of Ac-D-Trp + L-Naph-β-CD and that of Ac-L-Trp + L-Naph-β-CD complexes were practically the same due to common enthalpy-entropy compensation.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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