NSMDS: Molecular Design, Synthesis and Characterization of Green Glycolipid Surfactants

美国国家科学基金会化学部和环境保护局通过一个可持续分子设计和合成网络项目，支持珍妮·彭伯顿、沃尔特·克里梅基、雷纳·迈尔、罗宾·波尔特和史蒂文·施瓦茨教授在亚利桑那大学建立生物启发表面活性剂网络（NeBiS）。该网络结合了四位化学家、一位环境微生物学家和一位毒理学家的科学专业知识，系统地设计、合成和表征了一系列新的糖脂表面活性剂。最近发现的一种通用的、绿色的糖脂合成方法正被用来探索通过计算方法确定的目标糖脂的合成，这些目标糖脂在溶液和表面上具有优异的表面活性剂性质。综合战略涉及单变量绿色指标作为评估改进的定量基准，包括使用来自自然资源的可再生试剂。表面活性剂的溶液聚集行为通过一套全面的技术来确定临界胶束浓度和聚集体的形状和大小，部分与国家标准与技术研究所（NIST）的国家中子研究中心合作。表面活性剂的生物降解性是确定的，潜在候选物的毒性筛选是通过各种化学和生物试验进行的。在体外眼刺激模型中筛选有吸引力的靶点。这项工作将为表面活性剂的结构-功能关系提供新的见解，并推动分子设计的进步。表面活性剂是一种化合物，它可以降低液体的表面张力、两种液体之间的界面张力或液体与固体之间的界面张力。表面活性剂可以作为洗涤剂、润湿剂、乳化剂、发泡剂和分散剂。这些关键的、无处不在的化学物质存在于许多消费品和工业过程中，有着数十亿美元的市场。许多传统合成表面活性剂的毒性以及它们在环境中的持久性正在推动监管机构和消费者的压力，以开发更环保和更可持续的替代品。表面活性剂的无所不在，加上人们对其长期环境影响的日益关注，为绿色表面活性剂的分子设计和合成提供了一个引人注目的机会，特别是基于可再生材料的表面活性剂。在解决这个问题的同时，生物表面活性剂网络正在开展重要的教育和推广活动。这个多学科的项目为从博士后到高中生的广泛研究人员的跨学科培训提供了一个平台。研究生在可行的情况下接受共同指导，并要求在他们的研究中包括跨学科的组成部分。几名研究生与NIST的合作者一起参加了一个学期的实习。除了让高中教师和学生参与研究之外，正在开发以绿色化学为重点的新课程材料，其内容针对本科和高中水平。通过当地科学中心开展的外展活动针对的是K-12年级的学生，而通过科学卡姆斯的调查人员的参与，当地社区更广泛地参与到学习表面活性剂和绿色化学的活动中。

With this award, the NSF Division of Chemistry and the Environmental Protection Agency, through a program of Networks for Sustainable Molecular Design and Synthesis, support Professors Jeanne Pemberton, Walter Klimecki, Raina Maier, Robin Polt, and Steven Schwartz in establishing the Network for Bio-inspired Surfactants (NeBiS) at the University of Arizona. This network combines the scientific expertise of four chemists, an environmental microbiologist, and a toxicologist to systematically design, synthesize, and characterize a wide array of new glycolipid surfactants. The recent discovery of a versatile, green synthesis of glycolipids is being leveraged to explore the synthesis of target glycolipids identified by computational methods to possess excellent surfactant properties in solution and at surfaces. The synthetic strategy involves univariate green metrics as quantitative benchmarks for assessment of improvements, including the use of renewable reagents from natural resources. Solution aggregation behavior of surfactants is characterized with a comprehensive suite of techniques to determine critical micelle concentration and aggregate shape and size, in part in collaboration with the National Center for Neutron Research at the National Institute for Standards and Technology (NIST). The biodegradability of surfactants is determined, and the toxicity screening of potential candidates is carried out by a variety of chemical and biological assays. Attractive targets are screened in an in vitro model of ocular irritation. This effort will provide new insight into surfactant structure-function relationships and drive advances in molecular design. Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids or the interfacial tensions between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents and dispersants. These critical, ubiquitous chemicals are present in many consumer products and industrial processes, with a multi-billion-dollar market. The toxicity of many conventional synthetic surfactants as well as their persistence in the environment are driving regulatory and consumer pressure to develop greener and more sustainable alternatives.. The ubiquity of surfactants coupled with emerging concerns about their long-term environmental impacts, present a compelling opportunity for advances in molecular design and synthesis of green surfactants, particularly ones based upon renewable materials. While tackling this problem, the Network for Bio-inspired Surfactants is developing significant education and outreach activities. This multidisciplinary effort is a platform for the cross-disciplinary training of a broad spectrum of researchers, from postdoctoral researchers through high school students. Graduate students are co-mentored whenever feasible and are required to include a cross-disciplinary component in their research. Several graduate students participate in semester-long internships with collaborators at NIST. In addition to engaging high school teachers and students in research, new curricular materials focused on green chemistry are being developed with content targeted to undergraduate and high school levels. Outreach activities target K-12 students through the local Science Center, and the local community is engaged more broadly to learn about surfactants and green chemistry through the participation of the investigators in Science Cafés.