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1,5-脱水-D-果糖:制备、转化和衍生化的生物催化和化学合成方法。

1,5-Anhydro-D-fructose: biocatalytic and chemical synthetic methods for the preparation, transformation and derivatization.

机构信息

Department of Chemistry, Technical University of Denmark, Building 201, DK-2800 Kgs. Lyngby, Denmark.

出版信息

Carbohydr Res. 2010 Jan 26;345(2):181-90. doi: 10.1016/j.carres.2009.11.004. Epub 2009 Nov 6.

DOI:10.1016/j.carres.2009.11.004
PMID:20004890
Abstract

1,5-Anhydro-D-fructose (1,5AnFru) is a monoketosaccharide that can be prepared enzymatically from starch by alpha-1,4-glucan lyase or chemically from D-glucose or D-fructose in a few steps with high yields. The formed 1,5AnFru can be derivatized both enzymatically and chemically to interesting new carbohydrate derivatives, some with biological activities. For example dehydratases, isomerases and reductases can convert 1,5AnFru to enolones (as Ascopyrone P) and sugar alcohols with antimicrobial and antioxidant properties, while chemical modifications can give similar compounds as well as natural products like 1-deoxymannonojirimycin and Clavulazine. 1,5AnFru disaccharides (glycosyl 1-->4 1,5AnFru) have been prepared as well as glycosyl 1-->4 1,5-anhydro-D-tagatose.

摘要

1,5-脱水-D-呋喃果糖(1,5AnFru)是一种单酮糖,可以通过α-1,4-葡聚糖酶从淀粉中酶法制备,或者通过几步化学反应从 D-葡萄糖或 D-果糖以高产率制备。形成的 1,5AnFru 可以通过酶法和化学法进行衍生化,得到一些具有生物活性的有趣的新型碳水化合物衍生物。例如,脱水酶、异构酶和还原酶可以将 1,5AnFru 转化为烯酮(如 Ascopyrone P)和具有抗菌和抗氧化特性的糖醇,而化学修饰可以得到类似的化合物以及天然产物,如 1-去氧甘露诺乔米林和克拉维嗪。已经制备了 1,5AnFru 二糖(糖苷 1-->4 1,5AnFru)以及糖苷 1-->4 1,5-脱水-D-塔格糖。

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引用本文的文献

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The structure of substrate-free 1,5-anhydro-D-fructose reductase from Sinorhizobium meliloti 1021 reveals an open enzyme conformation.来自苜蓿中华根瘤菌1021的无底物1,5-脱水-D-果糖还原酶的结构揭示了一种开放的酶构象。
Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 Aug;69(Pt 8):844-9. doi: 10.1107/S1744309113019490. Epub 2013 Jul 27.
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Study on administration of 1,5-anhydro-D-fructose in C57BL/6J mice challenged with high-fat diet.1,5-脱水-D-果糖在高脂肪饮食诱导的 C57BL/6J 小鼠模型中的给药研究。
BMC Endocr Disord. 2010 Oct 19;10:17. doi: 10.1186/1472-6823-10-17.