1985
DOI: 10.1007/bf01412955
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The comparative spreading behavior of enantiomeric and racemic tyrosine amphiphiles

Abstract: Several derivatives of tyrosine or its methyl ester have been synthesized in which the para hydroxyl group on the aromatic side chain has been converted to a long chain alkyl ether or urethane. The surface behavior of these compounds is discussed. Enantiomeric discrimination, the ability of a chiral molecule to distinguish between mirror-image stereoisomers, has been investigated for the urethane derivates by comparing the surface pressure-area isotherms of the enantiomer with that of the racemic compound. Ena… Show more

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Cited by 13 publications
(10 citation statements)
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“…Π-A curves of the films over aqueous subphases were consistent with the literature data. [35][36][37] All of the films became more expanded over saturated dl-aspartic acid and d,l-asparagine monohydrate solutions, although this expansion effect was more marked for the l-tyrosine films. The expansion of the Π-A curves occurred up to surface pressures of approximately 20-25 mN m -1 ; above these surface pressures the films became condensed and attained the same limiting areas per molecule as found for the films over aqueous solutions (see Figure 2).…”
Section: Resultsmentioning
confidence: 99%
“…Π-A curves of the films over aqueous subphases were consistent with the literature data. [35][36][37] All of the films became more expanded over saturated dl-aspartic acid and d,l-asparagine monohydrate solutions, although this expansion effect was more marked for the l-tyrosine films. The expansion of the Π-A curves occurred up to surface pressures of approximately 20-25 mN m -1 ; above these surface pressures the films became condensed and attained the same limiting areas per molecule as found for the films over aqueous solutions (see Figure 2).…”
Section: Resultsmentioning
confidence: 99%
“… and had melting points of 197−198 °C and 163−164 °C, respectively. The NMR, infrared, and mass spectrometry data obtained from the film materials agreed with published data. …”
Section: Methodsmentioning
confidence: 99%
“…Materials. Film compounds were synthesized from the purest available starting materials: L-alanine octadecyl ester hydrochloride was synthesized following the procedure of Penney et al 30 and had a melting point of 112-114 °C; L-aspartic acid tetradecyl ester hydrochloride was synthesized following the procedure of Koch 31 and had a melting point of 109-111 °C; L-tyrosine O-octadecylcarbamoyl hydrochloride and its methyl ester were synthesized following the procedure of Marr-Leisy et al 32 and had melting points of 197-198 °C and 163-164 °C, respectively. The NMR, infrared, and mass spectrometry data obtained from the film materials agreed with published data.…”
Section: Methodsmentioning
confidence: 99%
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“…Daruber hinaus wird durch die Einfuhrung synthetischer Amphiphile die Moglichkeit geschaffen, Aggregate mit bestimmten Funktionen zu generieren 'I. Einen besonders interessanten Aspekt stellt in Anlehnung an native Phospholipide die Synthese chiraler Amphiphile dar. Bis heute ist nur wenig daruber bekannt, welchen Ein-flu0 ihre Chiralitat auf das Aggregationsverhalten und auf die Eigenschaften der gebildeten Aggregate ausiibt 6,7).…”
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