Anderson Arnold Aloanis, Tati Herlina, Ari Hardianto, Rani Maharani
{"title":"环烯galin A 的全合成。","authors":"Anderson Arnold Aloanis, Tati Herlina, Ari Hardianto, Rani Maharani","doi":"10.1002/open.202400175","DOIUrl":null,"url":null,"abstract":"<p><p>A Pro-Gly-typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid- and solution-phase synthetic methods. This study also compared the effectiveness of β-turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β-turn type I inducer (Ser-Ala-Val-Thr) as turning point and second sequence employed β-turn type II inducer (Thr-Pro-Gly-Leu). The successful cyclization was obtained using the linear sequence of NH<sub>2</sub>-Ala-Val-Thr-Pro-Gly-Leu-Ser-OH with β-turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR-ToFMS, <sup>1</sup>H NMR, <sup>13</sup>C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity.</p>","PeriodicalId":9831,"journal":{"name":"ChemistryOpen","volume":null,"pages":null},"PeriodicalIF":2.5000,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Total Synthesis of Cyclosenegalin A.\",\"authors\":\"Anderson Arnold Aloanis, Tati Herlina, Ari Hardianto, Rani Maharani\",\"doi\":\"10.1002/open.202400175\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A Pro-Gly-typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid- and solution-phase synthetic methods. This study also compared the effectiveness of β-turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β-turn type I inducer (Ser-Ala-Val-Thr) as turning point and second sequence employed β-turn type II inducer (Thr-Pro-Gly-Leu). The successful cyclization was obtained using the linear sequence of NH<sub>2</sub>-Ala-Val-Thr-Pro-Gly-Leu-Ser-OH with β-turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR-ToFMS, <sup>1</sup>H NMR, <sup>13</sup>C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity.</p>\",\"PeriodicalId\":9831,\"journal\":{\"name\":\"ChemistryOpen\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.5000,\"publicationDate\":\"2024-08-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemistryOpen\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/open.202400175\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistryOpen","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/open.202400175","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
我们首次从塞内加尔艳红和硬皮艳红中分离出一种 Pro-Gly 类型的环肽--环烯丙基肽 A。本研究采用固相和溶相相结合的合成方法合成了环七肽。本研究还比较了 I 型和 II 型β-转化诱导剂对环烯galin A 环化过程的促进作用。环烯galin A 的合成采用了两种不同的线性肽环化序列。第一种序列采用β-转Ⅰ型诱导剂（Ser-Ala-Val-Thr）作为转折点，第二种序列采用β-转Ⅱ型诱导剂（Thr-Pro-Gly-Leu）作为转折点。通过使用 NH2-Ala-Val-Thr-Pro-Gly-Leu-Ser-OH 与 β-转折型 II 的线性序列，成功实现了环化。以 PyBOP/DIEA 作为偶联剂，最终产物的收率为 8.2%。对合成的环烯galin A 进行了 HR-ToFMS、1H NMR、13C NMR、HSQC、HMBC、TOCSY 和 ROESY 表征。还对合成产品的抗菌活性进行了评估。
A Pro-Gly-typed cyclopeptide, cyclosenegalin A, was firstly isolated from Annona senegalensis and Annona scleroderma. In this study, we reported synthesis the cycloheptapeptide with a combination of solid- and solution-phase synthetic methods. This study also compared the effectiveness of β-turn inducer type I and II in cyclosenegalin A to facilitate the cyclization process. The synthesis of cyclosenegalin A were prepared using two different sequences of linear peptides for cyclization. First sequence employed β-turn type I inducer (Ser-Ala-Val-Thr) as turning point and second sequence employed β-turn type II inducer (Thr-Pro-Gly-Leu). The successful cyclization was obtained using the linear sequence of NH2-Ala-Val-Thr-Pro-Gly-Leu-Ser-OH with β-turn type II. The final product was obtained in 8.2 % yield with PyBOP/DIEA act as coupling agent. The synthetic cyclosenegalin A were characterized with HR-ToFMS, 1H NMR, 13C NMR, HSQC, HMBC, TOCSY, and ROESY. The synthetic product was also evaluated for its antimicrobial activity.
期刊介绍：
ChemistryOpen is a multidisciplinary, gold-road open-access, international forum for the publication of outstanding Reviews, Full Papers, and Communications from all areas of chemistry and related fields. It is co-owned by 16 continental European Chemical Societies, who have banded together in the alliance called ChemPubSoc Europe for the purpose of publishing high-quality journals in the field of chemistry and its border disciplines. As some of the governments of the countries represented in ChemPubSoc Europe have strongly recommended that the research conducted with their funding is freely accessible for all readers (Open Access), ChemPubSoc Europe was concerned that no journal for which the ethical standards were monitored by a chemical society was available for such papers. ChemistryOpen fills this gap.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
