Reverse Micellar Encapsulation of d- and l-Enantiomers of Some Aromatic α-Amino Acids and Nucleobases by Glucose-Derived Non-ionic Gemini

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• 作者：Lalit Sharma ; Saroj ; Nirmal Singh
• 关键词：Gemini surfactants ; Reverse micelles ; Amino acids ; Nucleobases ; 5 ; 6 ; Anhydromonoacetone glucose ; Encapsulation
• 刊名：Journal of Surfactants and Detergents
• 出版年：2015
• 出版时间：January 2015
• 年：2015
• 卷：18
• 期：1
• 页码：33-39
• 全文大小：304 KB
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  20. Wilk KA, Syper
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Industrial Chemistry and Chemical Engineering
  Surfaces and Interfaces and Thin Films
  Polymer Sciences
  Waste Water Technology, Water Pollution Control, Water Management and Aquatic Pollution
  Analytical Chemistry
  Physical Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1558-9293

文摘

Novel carbohydrate-based non-ionic gemini surfactants consisting of two sugar head groups, two hydrophobic tails having chain lengths of C12, C14, and C16 and a flexible -CH2)6-spacer were synthesized and investigated for their reverse micellar encapsulation properties. The head groups of the geminis comprise glucose entities (with reducing function blocked in a cyclic acetal group) connected through C-6 to tertiary amines. These surfactants were explored for reverse micellar encapsulation of d- and l-enantiomers of aromatic α-amino acids viz. histidine (His), phenylalanine (Phe), tyrosine (Tyr) and tryptophan (Trp) in neat n-hexane. Similar studies were carried out for encapsulation of nucleobases viz. adenine (Ade), guanine (Gua), thymine (Thy), cytosine (Cyt) and Uracil (Ura). Reverse micellar studies revealed that aromatic α-amino acids were encapsulated in the sequence His>Tyr>Phe>Trp. In most cases, a difference in the degree of encapsulation of d- and l-enantiomers of aromatic amino acids in reverse micellar phases of gemini amphiphiles in neat n-hexane, was revealed. For Tyr, l-enantiomer was better encapsulated than its antipode, i.e., d-enantiomer but for Trp, d-enantiomer was better encapsulated then l-enantiomer. In the case of nucleobases, Ura was found selectively encapsulated by reverse micelles formed by these new amphiphiles.