{"title":"揭开大自然抗氧化剂的神秘面纱:合成质体蛋白的新方法。","authors":"Jay Tromans, Bian Zhang, Bernard T Golding","doi":"10.1039/d4ob01233j","DOIUrl":null,"url":null,"abstract":"<p><p>Plasmalogens are glycerophospholipids distinguished by their <i>O</i>-(<i>Z</i>)-vinyl ether at the <i>sn</i>-1 position. These lipids are implicated in several disease states requiring analytical, diagnostic and therapeutic interventions, which demand synthetic availability for a variety of structural types. By deploying the new <i>O</i>-protecting group 1,4-dimethoxynaphthyl-2-methyl ('DIMON') and a new stereospecific method for accessing <i>Z</i>-vinyl ethers, a reproducible, versatile synthetic route to plasmalogens [plasmenyl phosphocholines] has been developed. A key intermediate is (<i>S</i>,<i>Z</i>)-1-((1,4-dimethoxynaphthalen-2-yl)methoxy)-3-(hexadec-1-en-1-yloxy)propan-2-ol, which in principle, permits plasmalogen synthesis 'à la carte' at scale. The methodology compares favourably with all previous synthetic routes by virtue of the very high configurational (>99% <i>Z</i>) and optical purity (>99% <i>ee</i>), including the ability to incorporate polyunsaturated fatty acyl chains (<i>e.g.</i> all <i>Z</i> docosahexaenoic acid) reliably at the <i>sn</i>-2 position.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Unlocking nature's antioxidants: a novel method for synthesising plasmalogens.\",\"authors\":\"Jay Tromans, Bian Zhang, Bernard T Golding\",\"doi\":\"10.1039/d4ob01233j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Plasmalogens are glycerophospholipids distinguished by their <i>O</i>-(<i>Z</i>)-vinyl ether at the <i>sn</i>-1 position. These lipids are implicated in several disease states requiring analytical, diagnostic and therapeutic interventions, which demand synthetic availability for a variety of structural types. By deploying the new <i>O</i>-protecting group 1,4-dimethoxynaphthyl-2-methyl ('DIMON') and a new stereospecific method for accessing <i>Z</i>-vinyl ethers, a reproducible, versatile synthetic route to plasmalogens [plasmenyl phosphocholines] has been developed. A key intermediate is (<i>S</i>,<i>Z</i>)-1-((1,4-dimethoxynaphthalen-2-yl)methoxy)-3-(hexadec-1-en-1-yloxy)propan-2-ol, which in principle, permits plasmalogen synthesis 'à la carte' at scale. The methodology compares favourably with all previous synthetic routes by virtue of the very high configurational (>99% <i>Z</i>) and optical purity (>99% <i>ee</i>), including the ability to incorporate polyunsaturated fatty acyl chains (<i>e.g.</i> all <i>Z</i> docosahexaenoic acid) reliably at the <i>sn</i>-2 position.</p>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-09-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob01233j\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01233j","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
质体磷脂是一种甘油磷脂,其特征在于 Sn-1 位置上的 O-(Z)- 乙烯基醚。这些脂质与多种疾病有关,需要进行分析、诊断和治疗干预,因此需要合成各种结构类型的脂质。通过使用新的 O 保护基团 1,4-二甲氧基萘-2-甲基("DIMON")和一种新的立体特异性方法来获得 Z-乙烯基醚,我们开发出了一种可重复的、多用途的质谱[plasmenyl phosphocholines]合成路线。一个关键的中间体是(S,Z)-1-((1,4-二甲氧基萘-2-基)甲氧基)-3-(十六-1-烯-1-基氧基)丙-2-醇,它原则上允许大规模 "点菜式 "合成质谱。该方法具有极高的构型纯度(Z 值大于 99%)和光学纯度(ee 值大于 99%),包括能够在 sn-2 位可靠地加入多不饱和脂肪酰基链(如全 Z 二十二碳六烯酸),因此优于以往所有的合成路线。
Unlocking nature's antioxidants: a novel method for synthesising plasmalogens.
Plasmalogens are glycerophospholipids distinguished by their O-(Z)-vinyl ether at the sn-1 position. These lipids are implicated in several disease states requiring analytical, diagnostic and therapeutic interventions, which demand synthetic availability for a variety of structural types. By deploying the new O-protecting group 1,4-dimethoxynaphthyl-2-methyl ('DIMON') and a new stereospecific method for accessing Z-vinyl ethers, a reproducible, versatile synthetic route to plasmalogens [plasmenyl phosphocholines] has been developed. A key intermediate is (S,Z)-1-((1,4-dimethoxynaphthalen-2-yl)methoxy)-3-(hexadec-1-en-1-yloxy)propan-2-ol, which in principle, permits plasmalogen synthesis 'à la carte' at scale. The methodology compares favourably with all previous synthetic routes by virtue of the very high configurational (>99% Z) and optical purity (>99% ee), including the ability to incorporate polyunsaturated fatty acyl chains (e.g. all Z docosahexaenoic acid) reliably at the sn-2 position.