N-Acyl tris(hydroxymethyl)aminomethanes (N-acyl tris, NATs) are structural analogs of ceramides, which were reported to induce apoptosis either by elevation of ceramide levels or by activation of pro-apoptotic effectors that are physiological targets of ceramide. In this study, we synthesized and characterized a homologous series of NATs bearing saturated acyl chains (n = 9–18) and investigated their supramolecular organization and thermotropic phase behavior. Transition enthalpies and entropies obtained from differential scanning calorimetric studies showed linear dependence on the chain length in both dry and hydrated states. The crystal structure of N-lauroyl tris (NLT), solved in monoclinic system in the P21/c space group, showed that owing to the bulky head group, NLT molecules pack in an interdigitated bilayer fashion. A number of OH⋯O and CH⋯O hydrogen bonds between the hydroxymethyl groups of the head groups of NLT molecules belonging to opposite layers as well as NH⋯O and CH⋯O hydrogen bonds between adjacent molecules belonging to the same layer, besides dispersion interactions between the all-trans hydrocarbon chains, stabilize the overall supramolecular organization of the self-assembled, interdigitated bilayer system. d-Spacings obtained from powder X-ray diffraction studies on all the NATs exhibited a linear dependence on the acyl chain length, suggesting that all of them adopt an interdigitated bilayer structure. These observations are relevant to developing structure-activity relationships for these amphiphiles and their analogs such as ceramides, N-acylserinols, N-acylalaninols and N-bis(2-hydroxyethyl)acylamides.

N-酰基三（羟甲基）氨基甲烷（N-酰基三，NAT）是神经酰胺的结构类似物，据报道它们通过神经酰胺水平的升高或激活作为神经酰胺的生理靶标的促凋亡效应子来诱导凋亡。在这项研究中，我们合成并表征了一系列带有饱和酰基链的NAT（n  = 9–18），并研究了它们的超分子组织和热致变相行为。从差示扫描量热法研究获得的跃迁焓和熵表明，在干燥和水合状态下，其链长均呈线性关系。N-月桂酰三（NLT）的晶体结构，在P21 / c单斜晶系中解析空间群表明，由于头部庞大，NLT分子以相互交叉的双层方式堆积。属于相对层的NLT分子的头基的羟甲基之间存在多个O H⋯O和C H⋯O氢键，以及属于同一层的相邻分子之间的N H⋯O和C H⋯O氢键除了全反式烃链之间的分散相互作用外，该层还稳定了自组装的叉指双层系统的整体超分子组织。d-从所有NAT的粉末X射线衍射研究获得的间距显示出对酰基链长度的线性依赖性，表明它们都采用了叉指状的双层结构。这些观察结果与这些两亲物及其类似物如神经酰胺，N-酰基鞘氨醇，N-酰基丙氨醇和N-双（2-羟乙基）酰基酰胺的结构-活性关系的发展有关。