N-acyl serinols, the amphiphilic molecules produced by gastrointestinal bacteria regulate metabolic hormone production and glucose homeostasis in the host species, and also exhibit anti-cancer activity. In this study, molecular structure, supramolecular organization and intermolecular interactions of two N-acylserinols (NASOHs), viz., N-nonanoylserinol (N9SOH) and N-pentadecanoylserinol (N15SOH), are determined by single-crystal X-ray diffraction. The molecular structure and packing are compared and discussed with the structurally related molecules, N-acylethanolamine (NAE) and N-acyl tris (NAT) as NASOHs and NATs are derived by substituting one/two α-hydrogen(s) (with respect to amide N-H) of NAE with hydroxymethyl group(s). Structures of N9SOH and N15SOH were solved in the triclinic system in the P-1 space group and both molecules are organized in a tilted head-to-head (and tail-to-tail) manner, resembling a bilayer membrane. The acyl chains in N9SOH and N15SOH are tilted by 20.43° and 18.12°, respectively, with respect to the bilayer normal. Several N—H⋯O, O—H⋯O, and C—H⋯O hydrogen bonds between the hydroxyl and amide moieties of the head groups of NASOH molecules belonging to adjacent and opposite layers stabilize the overall supramolecular organization. These results suggest that the α-hydroxymethyl groups exhibit considerable influence on the crystal structure, molecular packing, and phase structure of these amphiphiles.

Graphical abstract

Removing one of the CH₂OH moieties of N-acylserinol gives N-acylethanolamine, whereas introducing one more CH₂OH moiety on the α-carbon gives N-acyltris. While both N-acylethanolamine and N-acylserinol adopt tilted bilayer structure, the larger head group of N-acyltris induces it to adopt an interdigitated bilayer structure.

中文翻译：

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N-酰基丝氨醇的结构和超分子组织：G 蛋白偶联受体 GPR-119 的激动剂

N-酰基丝氨醇是胃肠道细菌产生的两亲性分子，可调节宿主物种的代谢激素产生和葡萄糖稳态，并且还具有抗癌活性。在这项研究中，两种N-酰基丝氨醇（NASOH）的分子结构、超分子组织和分子间相互作用，即。、N-壬酰丝氨醇（N9SOH）和N-十五酰丝氨醇（N15SOH）通过单晶X射线衍射测定。分子结构和堆积与结构相关的分子N-酰基乙醇胺 (NAE) 和N-酰基三 (NAT) 进行了比较和讨论，因为 NASOH 和 NAT 是通过取代一个/两个 α-氢而衍生的（相对于具有羟甲基的 NAE 的酰胺 NH)。N9SOH 和 N15SOH 的结构在P-1空间群的三斜晶系​​中得到解析，并且两个分子以倾斜的头对头（和尾对尾）方式组织，类似于双层膜。N9SOH和N15SOH中的酰基链相对于双层法线分别倾斜20.43°和18.12°。属于相邻和相对层的 NASOH 分子头基的羟基和酰胺部分之​​间的几个 N—H⋯O、O—H⋯O 和 C—H⋯O 氢键稳定了整个超分子组织。这些结果表明α-羟甲基对这些两亲物的晶体结构、分子堆积和相结构表现出相当大的影响。

图形概要

除去N-酰丝氨醇的CH ₂ OH部分之一得到N-酰基乙醇胺，而在α-碳上再引入一个CH _{2 OH部分得到}N-酰基三。虽然N-酰基乙醇胺和N-酰基丝氨醇均采用倾斜双层结构，但N -acyltris较大的头基导致其采用叉指式双层结构。