• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Design of Macrocyclic Multidentates Discriminating Molecular Chirality and Their Recognition Abilities

Research Project

Project/Area Number 13650903
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionOsaka University

Principal Investigator

NAKATSUJI Yohji  Osaka University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (00127268)

Co-Investigator(Kenkyū-buntansha) KIDA Toshiyuki  Osaka University, Graduate School of Engineering, Assistant Professor, 大学院・工学研究科, 助手 (20234297)
Project Period (FY) 2001 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2002: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2001: ¥2,700,000 (Direct Cost: ¥2,700,000)
KeywordsMolecular Recognition / Chiral Crown Ether / Complexation / クラウンエーテル / キラル認識 / リパーゼ触媒反応 / C_2-対称
Research Abstract

In this study, we developed a convenient synthetic procedure for C_2-symmetirc chiral crown ether having reactive hydroxyl groups and examined the chiral discrimination ability of the several C_2-symmetirc crown ether derivatives derived from the key intermediate toward primary ammonium salts. The results are summarized as follows.
1. As a preparative study for the development of chiral recognition host molecules based on the crown ether scaffold, the participation of the sidearm in the complexation with guest cations was examined by using several type of double armed lariat ethers. As a result, the introduction of the electron-donating sidearm to the crown ring was found to be highly effective in increasing the complexation ability toward alkali metal and alkaline earth metal cations.
2. A new convenient synthetic procedure for (S, S)-2, 12-bis(hydroxymethyl)-2, 12-dimethyl-18-crown-6 possessing plural reactive functional groups was developed.
3. Several types of sidearms such as naphthyloxymethyl, phenyloxymethyl, benzyloxymethyl, allyloxymethyl, and acectyloxymethyl were introduced to the 18 crown-6 ring by modification of the hydroxyl groups of (R, R)-2, 12 bis(hydroxymemyl)-2, 12-dimethyl-18-crown-6. The chiral recognition ability of the resulting crown ether derivatives toward (R) and (S) of the perchlorate salts of α-(1-naphtyl) ethylamine, α-phenylethylamine, and phenylglycinol was estimated by 1H-NMR titration method and the positive participation of the sidearm in the chiral recognition was observed.

Report

(3 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] Nakatsuji, Yohji: "Synthesis and Complexation Ability of a C-Pivot Type of Double-armed 15-Crown-5 Ethers toward Alkali Metal Cations"Bulletin of the Chemical Society of Japan. 75・8. 1765-1770 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Nakahara, Yoshio: "Fluorometric Sensing of Alkaline Earth Metal Cations by New Lariat Ethers Having Plural Pyrenylmethyl Groups on the Electron-donating Sidearms"Organic Letters. 4・16. 2641-2644 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yohji Nakatsuji, Masahiro Muraoka, Hiroyuki Kajiya, Wanbin Zhang, Toshiyuki Kida, and Isao Ikeda: "Synthesis and Complexation Ability of a C-Pivot Type of Double-armed 15-Crown-5 Ethers toward Alkali Metal Cations"Bull. Chem. Soc. Jpn.. 75 (8). 1765-1770 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yoshio Nakahara, Yasuo Matsumi, Wanbin Zhang, Toshiyuki Kida, Yohji Nakatsuji, and Isao Ikeda: "Fluorometric Sensing of Alkaline Earth Metal Cations by New Lariat Ethers Having Plural Pyrenylmettjyl Groups on the Electron-donating Sidearms"Org. Lett. 4 (16). 2641-2644 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Nakatsuji, Yohji: "Synthesis and Complexation Ability of a C-Pivot Type of Double-armed 15-Crown-5 Ethers toward Alkali Metal Cations"Bulletin of the Chemical Society of Japan. 75・8. 1765-1770 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Nakahara, Yoshio: "Fluorometric Sensing of Alkaline Earth Metal Cations by New Lariat Ethers Having Plural Pyrenylmethyl Groups on the Electron-donating Sidearms"Organic Letters. 4・16. 2641-2644 (2002)

    • Related Report
      2002 Annual Research Report

URL: 

Published: 2001-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi