{"title":"纤维素二糖磷酸化酶合成1,5-无水-4- o- β- d -葡萄糖吡喃基- d -果糖及其通过β-消除的自发分解。","authors":"Takahito Kajiki, Kazuhiro Yoshinaga, Shiro Komba, Motomitsu Kitaoka","doi":"10.5458/jag.jag.JAG-2017_010","DOIUrl":null,"url":null,"abstract":"<p><p>Cellobiose phosphorylase from <i>Cellvibrio gilvus</i> was used to prepare 1,5-anhydro-4-<i>O</i>-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.</p>","PeriodicalId":14999,"journal":{"name":"Journal of applied glycoscience","volume":null,"pages":null},"PeriodicalIF":1.2000,"publicationDate":"2017-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.5458/jag.jag.JAG-2017_010","citationCount":"3","resultStr":"{\"title\":\"Enzymatic Synthesis of 1,5-Anhydro-4-<i>O</i>-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination.\",\"authors\":\"Takahito Kajiki, Kazuhiro Yoshinaga, Shiro Komba, Motomitsu Kitaoka\",\"doi\":\"10.5458/jag.jag.JAG-2017_010\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Cellobiose phosphorylase from <i>Cellvibrio gilvus</i> was used to prepare 1,5-anhydro-4-<i>O</i>-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.</p>\",\"PeriodicalId\":14999,\"journal\":{\"name\":\"Journal of applied glycoscience\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.2000,\"publicationDate\":\"2017-11-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.5458/jag.jag.JAG-2017_010\",\"citationCount\":\"3\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of applied glycoscience\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.5458/jag.jag.JAG-2017_010\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2017/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of applied glycoscience","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.5458/jag.jag.JAG-2017_010","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2017/1/1 0:00:00","PubModel":"eCollection","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 3
摘要
利用来自gilvus Cellvibrio的纤维素二糖磷酸化酶，以1,5-无水d -果糖和α- d -葡萄糖1-磷酸为原料，制备了1,5-无水d -4- o- β- d - glucopyranoyl - d -fructose [βGlc(1→4)AF]。β- glc(1→4)AF通过β消除分解为d -葡萄糖和ascopyrone T。更高的pH值和温度导致更快的分解。然而，即使在温和的条件下，分解也会显著进行。例如，βGlc(1→4)AF在30℃、pH 7.0条件下的半衰期为17 h。由于βGlc(1→4)AF是纤维素的模拟物，其中C2羟基被氧化，因此这种分解在自然界中可能发生在氧化纤维素中。在这里，我们提出了一种可能的氧化途径。
Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination.
Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.
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