Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui
{"title":"小麦胚芽裂解物中亚精胺与甲基乙二醛糖基化模拟反应合成的新型四氢嘧啶化合物的鉴定","authors":"Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui","doi":"10.1016/j.tetlet.2025.155491","DOIUrl":null,"url":null,"abstract":"<div><div>Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155491"},"PeriodicalIF":1.5000,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers\",\"authors\":\"Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui\",\"doi\":\"10.1016/j.tetlet.2025.155491\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"157 \",\"pages\":\"Article 155491\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-02-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925000401\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/27 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925000401","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/27 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers
Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.