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

Synthesis of Pseudocyclophanes Bearing Multi-recognition Sites and the allosteric Control of Their Recognition Ability

Research Project

Project/Area Number 09640622
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionUniversity of Tsukuba

Principal Investigator

NABESHIMA Tatsuya  University of Tsukuba, Department of Chemistry, Associate Professor, 化学系, 助教授 (80198374)

Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1998: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1997: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsAllosteric Effect / Molecular Recognition / Cyclophane / Flavin / C-AMP / Bipyridine / Cu (I) Complex / c-AMP / アロステリ-
Research Abstract

In this study a new allosteric host was designed and synthesized. Allosteric host 1 consists of two 2,2'-bipyridine moieties, two bisphenol A skeletons, and an ammonium moiety. Host 1 binds a Cu(I) ion to give the corresponding tetrahedral complex, pseudocyclophane, which has a binding cavity and the ammonium group in close proximity. In solvent extraction, 1-Cu(I) complex showed a higher affinity toward flavin mononucleotide sodium salt (FMN) than 1. However, meaningful effect of Cu(I) is not found in a similar host, which does not have an ammonium moiety. These results strongly suggest that cooperative interactions between the cavity and the charged moiety of 1-Cu(I) are important for the FMN binding. After extraction of FMN with 1-Cu(I), the guest was moved to the aqueous phase again by the addition of bathocuproine or triethylamine hydrochloride. Bathocuproine strongly binds to Cu(I) to destroy 1-Cu(I) quantitatively. Triethylamine hydrochloride interacts with the guest to inhibit interaction between 1-Cu(I) and the phosphate moiety of the guest. These results indicated that the framework and the ammonium moiety of the pseudocyclophane are important for the recognition of the guest. In addition, the results show that on-and-off control of molecular recognition is achieved by using this system. A similar allosteric recognition of c-AMP was also performed successfully.
We believe that this study provided a new and fundamental way to construct a sophisticated on-and-off system for recognition of complicated organic molecules in artificial systems.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] Tatsuya Nabeshima: "On-and-off Control of Allosteric Affinity toward Flavin Mononucleotide by the Use of a Pseudoeyclophane Formed with Cu(I) as an Effector" J.Org.Chem.63. 2788-2789 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Tatsuya Nabeshima: "On-and-off Control of Allosteric Affinity toward Flavin Mononuclectide by the Use of a Pseudo cyclophane Formed with Cu (I) as an Effector" J.Org.Chem・. 63. 2788-2789 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Tatsuya Nabeshima: "On-and-off Control of Allosteric Affinity toward Flavin Mononucleatide by the Use of a Pseudecyclophane Formed with Cu(I) as an Effecter" J.Org.Chem.63. 2788-2789 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 鍋島達弥: "On-and-off Control of Allosteric Affinity toward Flavin Mononucleotide by the Use of a Pseudocyclophane Formed with Cu(I) as an Effector" J.Org.Chem.63(印刷中). (1998)

    • Related Report
      1997 Annual Research Report

URL: 

Published: 1997-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi