Effect of Stereochemistry on the Molecular Aggregation of Phenylalanine Dipeptide-type Surfactants
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- Ohta Akio
- Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
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- Shirai Mari
- Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
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- Asakawa Tsuyoshi
- Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
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- Miyagishi Shigeyoshi
- Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University
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Abstract
The aggregation behaviors of three stereoisomers of tetramethylammonium N-dodecanoyl phenylalanylphenylalaninate in dilute aqueous solution were investigated. From surface tension, fluorescence intensity using probes, and heat of dilution measurements, it was suggested that the critical aggregation concentration was the same between the enantiomers, but was obviously different between the diastereomers. It was also found that these surfactants formed large aggregates at lower concentrations. These large aggregates were then transformed to micelles at higher concentrations similarly to the potassium N-acyl phenylalaninate system. Furthermore, the fluorescence intensity of auramine increased strikingly in the N-dodecanoyl-L-phenylalanyl-L-phenylalanine (homo-chiral dipeptide-type surfactant) system. The fluorescence intensity of auramine in the aggregate of homo-chiral dipeptide-type surfactant was 20 times larger than that in the hetero-chiral dipeptide-type surfactant.
Journal
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- Journal of Oleo Science
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Journal of Oleo Science 57 (12), 659-667, 2008
Japan Oil Chemists' Society
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Keywords
Details 詳細情報について
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- CRID
- 1390282679069182592
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- NII Article ID
- 130000435864
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- NII Book ID
- AA11503337
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- ISSN
- 13473352
- 13458957
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- NDL BIB ID
- 9708844
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed