Structure and supramolecular organization of N-acylserinols: agonists of the G-protein coupled receptor, GPR-119

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Suman K Choudhury, D Sivaramakrishna, Musti J Swamy
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引用次数: 0

Abstract

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.

Abstract Image

n -酰基丝氨酸醇的结构和超分子组织:g蛋白偶联受体GPR-119的激动剂
n -酰基丝氨酸醇是胃肠道细菌产生的两亲分子,可调节宿主体内代谢激素的产生和葡萄糖稳态,并具有抗癌活性。本研究利用单晶x射线衍射测定了n -壬烷基丝氨酸醇(N9SOH)和n -五烷基丝氨酸醇(N15SOH)两种n -酰基丝氨酸醇(NASOHs)的分子结构、超分子组织和分子间相互作用。与结构相关分子n -酰基乙醇胺(NAE)和n -酰基三醇胺(NAT)的分子结构和排列进行了比较和讨论,NASOHs和NATs是由NAE的1 / 2个α-氢(相对于酰胺N-H)取代羟基(s)而得到的。N9SOH和N15SOH的结构在P-1空间基团的三斜体系中被解析,两种分子以倾斜的头对头(和尾对尾)的方式组织,类似于双层膜。N9SOH和N15SOH中的酰基链相对于双分子层正线分别倾斜20.43°和18.12°。几个N-H⋯O, O - h⋯O和C-H⋯O氢键在NASOH分子的羟基和酰胺基团之间,属于相邻和相反的层,稳定了整个超分子组织。结果表明,α-羟甲基对两亲体的晶体结构、分子堆积和相结构有较大的影响。图摘要:去掉n -酰基丝氨酸醇的一个CH2OH基团得到n -酰基乙醇胺,而在α-碳上再引入一个CH2OH基团得到n -酰基三聚体。n -酰基乙醇胺和n -酰基丝氨酸醇均采用倾斜的双层结构,但n -酰基三聚体头部基团较大,导致其采用交错的双层结构。
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来源期刊
Journal of Chemical Sciences
Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.10
自引率
5.90%
发文量
107
审稿时长
1 months
期刊介绍: Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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