论文标题
氨基和藻类的合成和自组装取代
Synthesis and self-assembly of aminyl and alkynyl substituted sophorolipids
论文作者
论文摘要
Sophorolipids是最重要的微生物生物效果剂之一,因为它们的大规模生产和迄今为止在洗涤剂,微生物学,化妆品或环境科学领域发展。但是,本机sophorolipids的结构变化是有限/受限的,这是开发新属性及其潜在应用的限制事实。 C18:1 sophorolipids(SL)在其开放式酸性形式中是由柔软的头组和羧酸(COOH)末端组组成的。羧基赋予它们独特的pH响应性能,但它们是一个反应不良的群体,其电荷只能为负。为了开发新一代的pH响应性,充电,SL并提高其反应性以进一步功能化,我们在这里使用胺(-NH2)或末端碱(-c $ \ not \ equiv $ ch)终端类似物开发SLS。胺组产生呈阳性的SL,并且比羧酸更具反应性,例如朝向醛; Alkyne组可访问基于铜的点击化学。在这项工作中,我们合成(C18:1)和(C18:0)-NH2和(C18:1)-c $ \ not \ equiv $ ch sophorolipid衍生物,我们研究其自组装特性,响应于pH和/或通过静态和动态光散射,小角度(x ray,x ray,netronic,netication)响应pH和/或温度变化。单不饱和的氨基SL-C18:1-NH2 Sophorolipids在高pH下以其中性形式形成胶束相,在低pH下以阳性的形式形式的混合胶束 - 双层相。饱和的氨基氨基-C18:0-NH2 sophorolipids在低pH值下以带电形式形成胶束相,并在高pH值和单一饱和的酸性Alkynyl sl-c18:1-c $ \ equiv $ ch $ ch sophorolipid形成t trip> 51.8 c \ texteeg cribor case and> 51.8 c \ crepare sophorolipid的中性形式和中性形式的扭曲色带相位。 51.8 {\ textDegree} c。
Sophorolipids are one of the most important microbial biosurfactants, because of their large-scale production and applications developed so far in the fields of detergency, microbiology, cosmetics or environmental science. However, the structural variety of native sophorolipids is limited/restricted, a limiting fact for the development of new properties and their potential applications. In their open acidic form, C18:1 sophorolipids (SL) are classically composed of a sophorose headgroup and a carboxylic acid (COOH) end-group. The carboxyl group gives them unique pH-responsive properties, but they are a poorly-reactive group and their charge can only be negative. To develop a new generation of pH-responsive, positively-charged, SL and to improve their reactivity for further functionalization, we develop here SLs with an amine (-NH2) or terminal alkyne (-C$\not\equiv$CH) end-group analogues. The amine group generates positively-charged SL and is more reactive than carboxylic acids, e.g. towards aldehydes; the alkyne group provides access to copper-based click chemistry. In this work, we synthesize (C18:1) and (C18:0) --NH2 and (C18:1) -C$\not\equiv$CH sophorolipid derivatives and we study their self-assembly properties in response to pH and/or temperature changes by means of static and dynamic light scattering, small angle (X-ray, neutron) scattering and cryogenic electron microscopy. Monounsaturated aminyl SL-C18:1-NH2 sophorolipids form a micellar phase in their neutral form at high pH and a mixed micellar-bilayer phase in their positively-charged form at low pH. Saturated aminyl SL-C18:0-NH2 sophorolipids form a micellar phase in their charged form at low pH and a twisted ribbon phase in their neutral form at high pH and monounsaturated alkynyl SL-C18:1-C$\not\equiv$CH sophorolipids form a main micellar phase at T> 51.8{\textdegree}C and a twisted ribbon phase at T< 51.8 {\textdegree}C.