{"title":"含有交替的 C-糖基 α-氨基酸和蛋白源 α-氨基酸的低聚物的合成","authors":"Ivana Colić, Barbara Bogović and Ivanka Jerić","doi":"10.1039/D4NJ02059F","DOIUrl":null,"url":null,"abstract":"<p >\r\n <em>C</em>-Glycosyl amino acids are a group of <em>C</em>-glycosides in which a carbohydrate molecule is attached to the side chain or backbone of the amino acid <em>via</em> a C–C bond. Despite the numerous methods that have been developed for their synthesis, the <em>C</em>-glycosyl α-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating <em>C</em>-glycosyl α-amino acids and proteinogenic α-amino acids. The methodology is based on the modification of α-acyloxyamides obtained from the Passerini reaction using α-<small>D</small>-galactopyranose- and α-<small>L</small>-sorbofuranose-derived aldehydes as <em>C</em>-glycosyl donors. The protocol enabled the synthesis of homo- and heterochiral tetramers, and homo- and heterovalent tetramers in very good yields.</p>","PeriodicalId":95,"journal":{"name":"New Journal of Chemistry","volume":null,"pages":null},"PeriodicalIF":2.7000,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/nj/d4nj02059f?page=search","citationCount":"0","resultStr":"{\"title\":\"The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids†\",\"authors\":\"Ivana Colić, Barbara Bogović and Ivanka Jerić\",\"doi\":\"10.1039/D4NJ02059F\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >\\r\\n <em>C</em>-Glycosyl amino acids are a group of <em>C</em>-glycosides in which a carbohydrate molecule is attached to the side chain or backbone of the amino acid <em>via</em> a C–C bond. Despite the numerous methods that have been developed for their synthesis, the <em>C</em>-glycosyl α-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating <em>C</em>-glycosyl α-amino acids and proteinogenic α-amino acids. The methodology is based on the modification of α-acyloxyamides obtained from the Passerini reaction using α-<small>D</small>-galactopyranose- and α-<small>L</small>-sorbofuranose-derived aldehydes as <em>C</em>-glycosyl donors. The protocol enabled the synthesis of homo- and heterochiral tetramers, and homo- and heterovalent tetramers in very good yields.</p>\",\"PeriodicalId\":95,\"journal\":{\"name\":\"New Journal of Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2024-06-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.rsc.org/en/content/articlepdf/2024/nj/d4nj02059f?page=search\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"New Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02059f\",\"RegionNum\":3,\"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":"New Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/nj/d4nj02059f","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids†
C-Glycosyl amino acids are a group of C-glycosides in which a carbohydrate molecule is attached to the side chain or backbone of the amino acid via a C–C bond. Despite the numerous methods that have been developed for their synthesis, the C-glycosyl α-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids. The methodology is based on the modification of α-acyloxyamides obtained from the Passerini reaction using α-D-galactopyranose- and α-L-sorbofuranose-derived aldehydes as C-glycosyl donors. The protocol enabled the synthesis of homo- and heterochiral tetramers, and homo- and heterovalent tetramers in very good yields.