Understanding how the diversity of glycolipids, including how their chemical structures and composition affect their biological functions, is a remarkable fundamental challenge. In this work, we employed a rare monosaccharide, 3-deoxy-d-manno-2-octulosonic acid (Kdo) to build a simple and biomimetic model to understand the diversity of glycolipids from the viewpoint of supramolecular chemistry. Kdo was chosen not only because its unusual 8-carbon acidic carbohydrate backbone is very different from common hexoses, but also because of its key structural role in lipopolysaccharides and prevalence in bacteria, plant life, and algae. It was found that although both of the two Kdo-lipids S-Kdo and Kdo-S derived from the same carbohydrate backbone and gave bicelles as their self-assembled morphology, experimental results revealed that the self-assembly showed pathway complexity. Bicelle is the thermodynamic product of S-Kdo, while for Kdo-S, the bicelle is only a kinetically trapped state, which finally transforms to a ribbon. Molecular simulation clearly revealed the different packing of Kdo-lipids in the bicelles with different contribution from hydrogen bonds and electrostatic interactions.

了解糖脂的多样性，包括它们的化学结构和组成如何影响其生物学功能，是一项重大的基本挑战。在这项工作中，我们采用了一种稀有单糖，3-脱氧d -manno -2-辛酮糖酸（KDO），以建立一个简单的和仿生模型，以了解糖脂的从超分子化学的观点出发的多样性。选择 Kdo 不仅是因为其不寻常的 8 碳酸性碳水化合物主链与常见的己糖非常不同，还因为它在脂多糖中的关键结构作用以及在细菌、植物和藻类中的流行。发现虽然这两种 Kdo-lipids S-Kdo 和 Kdo-S源自相同的碳水化合物主链并给出了双细胞作为它们的自组装形态，实验结果表明自组装显示出途径的复杂性。Bicelle 是热力学积 S-Kdo, 而对于 Kdo-S，bicelle 只是一种动力学捕获状态，最终转变为带状。分子模拟清楚地揭示了双胞胎中 Kdo-脂质的不同堆积，具有不同的氢键和静电相互作用贡献。