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1990 Fiscal Year Final Research Report Summary

Development of Selective Synthetic Reactions of Sugars Based on Their Complexation.

Research Project

Project/Area Number 01470094
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionNagaoka University of Technology

Principal Investigator

AOYAMA Yasuhiro  Nagaoka Univ. of Technology Dept. of BioEngineering, Dr. Prof., 工学部, 教授 (00038093)

Co-Investigator(Kenkyū-buntansha) KOBAYASHI Kenji  Nagaoka Univ. of Technology Dept. of Bioengineering, Dr. Research Assoc., 工学部, 助手 (40225503)
TOI Hiroo  Nagaoka Univ. of Technology Dept. of BioEngineering, Dr. Assoc. Prof., 工学部, 助教授 (90126475)
Project Period (FY) 1989 – 1990
Keywordssugars / hydrogen bonding / host-guest / molecular recognition / circular dichroism
Research Abstract

(1) Development of Selective Synthetic Reactions of Sugars.
Ribose solubilized in carbon tetrachloride via hydrogen-bonding complexation with resorcinolaldehyde cyclotetramer was found to undergo methylation with methanol to give methyl betaribofuranoside highly stereoselectively.
(2) Molecular Recognition of Sugars via Hydrogen-Bonding.
Resorcinol-aldehyde cyclotetramer was found to discriminate slight structural differences in sugars in their hydrogen-bonding fixation. It was thus possible to differentiate fructose vs glucose and alpha anomer of methyl glucopyranoside from the beta anomer.
(3) Determination of Sugar Conformation Based on Induced Circular Dichroism.
The sugar complexes of resorcinol-aldehyde cyclotetramer exhibit circular dichroism with split Cotton effects. The signs of the Cotton effects could be correlated with the conformation of the sugar, wither C1 or 1C.
(4) Development of a New Class of Sugar Binder.
A new class of macrocycle based on an octaazamacrocycle was prepared. It was functionalized by eight long-alkyl chains having polar OH groups. This macrocycle in chloroform was found to extract various polar materials including sugars from water. Not only monosaccharides (glucose and fructose) but also disaccharides could be solubilized in this manner.
This work thus opens the door to an entirely new field of sugar chemistry, based on apecific host-guest interactions in apolar organic media. This concept can be applied to the synthetic, analytical, structural, and organic aspects of the sugars.

  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Yasuhiro Aoyama: "Molecular Recognition.5.Mlecular Recognition of Sugars via HydrogenーBonding Interaction with a Synthetic Polyhydroxy Macrocycle." J.Am.Chem.Soc.111. 5397-5404 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasutaka Tanaka: "Selective Sugar Binding with a Synthetic Polyhydroxy Macrocycle. A Remarkable Selectivity for Fructose over Glucose." Chem. Lett.1905-1908 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasutaka Tanaka: "Highly Stereoselective Glycosidation of Ribose Solubilized in Apolar Organic Media via HostーGuest Complexation." Tetrahedron Lett.31. 6193-6196 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sutarto Supriyanto: "Molecular Recognition of Sugar Glycosides. A Remarkable Diastereoselectivity in the binding of Anomeric Methyl Glucopyranosides witj ResorcinolーAldehyde Cyclotetramer." Angew.Chem.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kenji Kobayashi: "Molecular Recognition of Galactose Derivatives in the Complexation with ResorcinolーAldehyde Cyclotetramer via Multipoint HydrogenーBonding" Bull.Chem.Soc.Jpan.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kenji Kobayashi: "Solubilization of Sugars in Apolar Organic Media via Microsolvation Effect." J.Am.Chem.Soc.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Aoyama, et. al.: "Molecular Recognition of Sugars via Hydrogen-Bonding Interaction with a Synthetic Polyhydroxy Macrocycle" J. Am. Chem. Soc.111. 5397-5404 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, Et. al.,: "Selective Sugar Binding with a Synthetic Polyhydroxy Macrocycle. A Remarkable Selectivity for Fructose over Glucose" Chem. Lett. 1905-1908 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, et. al.,: "Highly Stereoselective Glycosidation of Ribose Solubilized in Apolar Organic Media via Host-Guest Complexation" Tetrahedron Lett. 31. 6193-6196 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, et. al.,: "Molecular Recognition of Sugar Glycosides. A Remarkable Diastereoselectivity in the Binding of Anomeric Methyl Glucopyranosides with Resorcinol-Aldehyde Cyclotetramer" Angew. Chem.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, et. al.,: "Molecular Recognition of Galactose Derivatives in the Complexation with Resorcinol-Aldehyde Cyclotetramer via Multipoint Hydrogen-Bonding." Bull. Chem. Soc. Jpn.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, et. al.,: "Solubilization of Sugara in Apolar Organic Media via Microsolvation Effect" J. Am. Chem. Soc.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Aoyama, et. al.,: "Complexation of Chiral Vicinal Diols, Sugars, and Steroidal Polyols as Studied by Induced Circular Dichroism : Resorcinol-Aldehyde Cyclotetramer as a Supramolecular Probe for the Assignments of Stereochemistry" J. Am. Chem. Soc.

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1993-08-12  

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