Novel glucose derived non-ionic gemini surfactants as reverse micellar systems for encapsulation of d- and l-enantiomers of some aromatic α-amino acids in n-hexane
作者:Lalit Sharma、Saroj
DOI:10.1007/s10847-012-0107-y
日期:2012.12
Novel glucose-based non-ionic gemini amphiphiles comprising two sugar head groups, two hydrophobic tails having chain length of C12, C14, and C18 and a –CH2–Ar–CH2– spacer have been synthesized. The head groups of the geminis consist of glucose entities (with reducing function blocked in cyclic acetal group) connected through C-6 to tertiary amines. These amphiphiles were explored as reverse micellar systems, for the encapsulation of d- and l-enantiomers of ultraviolet-absorbing aromatic α-amino acids histidine (H), phenylalanine (F), tyrosine (Y) and tryptophan (W) in n-hexane, without any added water. Reverse micellar studies revealed that aromatic α-amino acids were encapsulated in the sequence H > F > Y > W. In most cases, specifically for F, d-enantiomer was found better encapsulated than l-enantiomer in the reverse micellar probes of the gemini surfactants.
合成了一种新型的基于葡萄糖的非离子双子表面活性剂,这些表面活性剂由两个糖头基、两条具有C12、C14和C18链长的疏水尾巴以及一个–CH2–Ar–CH2–间隔组成。双子表面活性剂的头基由葡萄糖实体组成(还原功能被环缩醛基团封闭),通过C-6连接到三级胺。这些表面活性剂被用于反向胶束体系中,封装紫外线吸收的芳香α-氨基酸组氨酸(H)、苯丙氨酸(F)、酪氨酸(Y)和色氨酸(W)的d-和l-对映体,且没有添加任何水。反向胶束研究表明,芳香α-氨基酸的封装顺序为H > F > Y > W。在大多数情况下,特别是对于F,发现d-对映体在双子表面活性剂的反向胶束中封装得比l-对映体更好。