Abstract
Non-ionic carbohydrate based gemini surfactants with rigid aromatic spacer CH2-Ar-CH2, which carry two hydrophobic tails of different tail lengths (C12, C14 and C16) and two sugar moiety polar head groups were synthesized and their reverse micellar behavior for solubilization of some aromatic α-amino acids viz. histidine (His), phenylalanine (Phy), tyrosine (Tyr) and tryptophan (Trp) in n-hexane were studied by spectroscopic analysis. The head group of these gemini surfactants consists of sugar moiety connected to C-6 of tertiary amines. Amino acids form complexes in order of His > Phy > Tyr > Trp, and in all cases it was found that the D-enantiomers solubilize better in comparison to the L-enantiomers. Moreover, more hydrophobic surfactants i.-e. surfactants with longer hydrocarbon tails show greater complex formation tendency towards D- and L-enantiomers of aromatic α-amino acids.
Kurzfassung
Nichtionische Gemini-Tenside auf Kohlenhydratbasis mit starrem aromatischem Spacer CH2-Ar-CH2, die zwei unterschiedlich lange hydrophobe Schwänze (C12, C14 und C16) und zwei polare Kopfgruppen der Zuckereinheit tragen, wurden synthetisiert. Ihr umgekehrtes mizellares Verhalten zur Solubilisierung einiger aromatischer α-Aminosäuren, nämlich Histidin (His), Phenylalanin (Phy), Tyrosin (Tyr) und Tryptophan (Trp) in n-Hexan wurde durch spektroskopischen Methoden analysiert. Die Hauptgruppe dieser Geminitenside besteht aus einer Zuckereinheit, die an C-6 der tertiären Amine gebunden ist. Die Aminosäuren bilden Komplexe in der Reihenfolge von His > Phy > Tyr > Trp, und es wurde in allen Fällen festgestellt, dass die D-Enantiomere im Vergleich zu den L-Enantiomeren besser solubilisieren. Darüber hinaus zeigen hydrophobere Tenside, d.-h. Tenside mit längeren Kohlenwasserstoffschwänzen, eine größere Tendenz zur Komplexbildung gegenüber den D- und L-Enantiomeren von aromatischen α-Aminosäuren.
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