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Synthesis of the peptide-surfactants containig an optical active biphenyl-unit and their use for the assymetric synthesis.

Research Project

Project/Area Number 60550616
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionToa University

Principal Investigator

NAKANO Akio  Faculty of Engineering, Toa University, 工学部, 助教授 (90091355)

Project Period (FY) 1985 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1986: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1985: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsSurfactant / Bilayer-membrane / Optical-selectivity / Biphenyl-compound / 加水分解 / ビタミン【B_6】
Research Abstract

Two kinds of the peptide-surfactants which include an optical active biphenyl-unit were synthesized and the physical properties of their aggregates were investigated. Electron micrographs of their aggregates indicate that the aqueous dispersion of cationic surfactant containig a biphenyl-unit apparently involves multiwalled lamellae and vesicles and also that the multi-walled aggregates is completly converted into the single-walled vesicles upon sonication of this aqueous dispersion. These aggregate-structures bear a close resemblance to those formed with the phospholipids. The phase transition parameters obtained for these peptide-surfactants were similar to the values obtained for the ones employed before. The fact suggests that these surfactants are able to form a tight hydrogen-belt in their aggregates. The hydrolysis of enantiomeric esters of various hydrophobic nature, which was carried out by using a mixed membrane systems composed with the surfactants synthesized in this work, showed relatively small enantioselectivity. The biphenyl-unit is so bulky that the interaction between the reaction-site of the substrate and the histidyl residue which is adfacent to the biphenyl group might be largely reduced. In conclusion, the cationic peptide surfactant containing biphenyl-unit in addition to the reactive group (histidine) should be synthesized and employed for the catalytic systems of Vitamin <B_6> .

Report

(1 results)
  • 1986 Final Research Report Summary

URL: 

Published: 1987-03-31   Modified: 2016-04-21  

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