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

1996 Fiscal Year Final Research Report Summary

Functional Molecular Assemblies Coupled to Steric Control with High Enantioselectivity

Research Project

Project/Area Number 07650968
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 生物・生体工学
Research InstitutionKumamoto Institute of Technology

Principal Investigator

UEOKA Ryuichi  Kumamoto Institute of Technology, Industrial Chemistry, Professor, 工学部, 教授 (70099076)

Co-Investigator(Kenkyū-buntansha) SAKOGUCHI Akihiro  Kumamoto Institute of Technology, Industrial Chemistry, Lecturer, 工学部, 講師 (30196141)
MATSUMOTO Yoko  Kumamoto Institute of Technology, Industrial Chemistry, Associate Professor, 工学部, 助教授 (00133562)
Project Period (FY) 1995 – 1996
KeywordsFunctional Molecular Assembly / Asymmetric Reaction / Stereoselectivity / Amino Acid Ester / Optical Resolution / Supramolecular Chemistry / Steric Control / Molecular Recognition
Research Abstract

Enantioselective hydrolysis of amino acid esters by L-histidine derivatives in the molecular assemblies composed of single-and double-chain surfactants was investigated. The noteworthy aspects are as follows :
1) The remarkably high enantioselectivity (kappa^L_<a, obsd>/kappa^D_<a, obsd>=1000) was sttained for the hydrolysis of longchained substrate (N-dodecanoyl-D (L) -phenylalanine p-nitrophenylester ; C_<12>-D (L) -Phe-PNP) catalyzed by the active tripeptide (N-(benzyloxycarbonyl) -L-phenylalanyl-L-histidyl-L-leucine ; Z-PheHisLeu) in the coaggregate systems composed of 41mol% single-chained hexadecyltrimethylammonium bromide (CTAB) and 59mol% double-chained ditetradecyldimethylammonium bromide (2C_<14>Br) at the specific ionic strength (mu=0.02).
Furthermore, the computer modeling (MOPAC calculation) study suggests that a favorable molecular recognition between the substrate and the catalyst through the effective hydrophobic interactions and hydrogen bonds should be very important for the enhancement of enantioselectivity.
2) With respect to the hydrolysis of C_<12>-D (L) -Phe-PNP by the tripeptide catalyst Z-PheHisLeu in the coaggregate systems composed of native lipid and nonionic micellar surfactant, a remarkably high enantioselectivity (kappa^L_<a, obsd>/kappa^D_<a, obsd>=28) along with marked rate-enhancement of the hydrolytic cleavage of C_<12>-D (L) -Phe-PNP was obtained with specific coaggregates of 32mol% L-alpha-dipalmitoylphosphatidyl-choline (DPPC) and 68mol% alpha-[4-(1,1,3,3-tetramethylbutyl) phenyl]-omega-hydroxypoly (exy-1,2-ethanediyl) (Triton X-100). The enantioselectivity was maximized at the phase transition temperature (Te) in the 65mol% DPPC/35mol% Triton X-100 and 32mol% DPPC/68mol% Triton X-100 coaggregate systems. The hydrophobicity and fluidity of the coaggregates can apparently be changed around Te on the basis of isokinetic temperature and fluorescence parameter studies.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] 後藤浩一: "機能性分子集合体を用いたアミノ酸エステル基質の不斉加水分解反応" 日本化学会誌. 1997・2. 127-133 (1997)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ryuichi Ueoka: "A Remarkably Enhanced Diastereo selectirity for the Hydrolysis" Tetrahedron Letters. 37・20. 3461-3464 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ryuichi Ueoka: "Liguid Membranes for the Hydrdysis of Amino Acid Esters" Proceeding of International Sdvent Extraction Conference. 2. 953-958 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Koichi Goto: "Hybrid Liposomes Coupled to Steric Control" The Journal of Organic Chemistry. 60・11. 3342-3346 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 上岡龍一: "超分子集合体を用いた分子認識機能の発現" 化学工学シンポジウムシリーズ54. 51-61 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 上岡龍一: "超分子化学の基礎と応用" (株)エヌ・ティー・エス, 623 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Koichi GOTO: "Molecular Recognition for the Enantioselective Hydrolysis of Amino Acid Esters in Functional Molecular Assembly Systems" NIPPON KAGAKU KAISHI. No. 2. 127-133 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ryuichi Ueoka: "A Remarkably Enhanced Diastereoselectivity for the Hydrolysis of Dipeptide Esters Responding to pH and Temperature in Buffer Solutions" Tetrahedron Letters. Vol. 37, No. 20. 3461-3464 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ryuichi Ueoka: "Liquid Membranes for the Hydrolysis of Amino Acid Esters and the Inhibition of Tumor Promotion in Vitro" Proceeding of International Solvent Extraction Conference '96. Vol. 12. 953-958 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ryuichi Ueoka: "Molecular Recognition in Supramolecular Assemblies" Chemical Engineering Symposium Series. 54. 51-61 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Koichi Goto: "Hybrid Liposomes Coupled to Steric Control with High Enantioselectivity" The Journal of Organic Chemistry. Vol. 60, No. 11. 3342-3346 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ryuichi Ueoka: Supramolecular Chemistry -basic concepts and recent advances-. NTS Co., Inc, 623 (1996)

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

URL: 

Published: 1999-03-09  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi