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

被引:9
作者
Lundt, Inge [1 ]
Yu, Shukun [2 ]
机构
[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
[2] Danisco AS, Genencor, Dept Enzyme Dev, DK-8220 Aarhus, Denmark
关键词
1,5-Anhydro-D-fructose; Enzymatical synthesis; Chemical synthesis and properties; Enzymatical and chemical modification of 1,5-anhydro-D-fructose; 1,5-Anhydro-D-fructose disaccharides; 1,5-Anhydro-D-tagatose disaccharides; ACTIVITY DEGRADING 1,4-ALPHA-D-GLUCANS; CHIRAL BUILDING-BLOCK; ALPHA-1,4-GLUCAN LYASE; ANHYDROFRUCTOSE PATHWAY; ASCOPYRONE-P; EFFICIENT PURIFICATION; ENZYMATIC DESCRIPTION; GLYCOGEN DEGRADATION; CONVENIENT ACCESS; D-GLUCOSE;
D O I
10.1016/j.carres.2009.11.004
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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. (C) 2009 Elsevier Ltd. All rights reserved.
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页码:181 / 190
页数:10
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