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Chemical Compound Review:

SureCN246685 (4S,5S,6R)-4,5-dihydroxy-6...

Synonyms: KST-1B8624, AC1Q6ETX, AR-1B8018, AC1L2QH3, C06485, ...

Dambe, T.R. et al., Taguchi, T. et al., Yamaji, K. et al., Yu, S. et al., Deppe, O. et al., et al.

Deppe, Glümer, Yu, Buchholz, Yamaji, Sarker, Maruyama, Hizukuri,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of 1,5-Anhydro-D-fructose

Crystal structure of NADP(H)-dependent 1,5-anhydro-D-fructose reductase from Sinorhizobium morelense at 2.2 A resolution: construction of a NADH-accepting mutant and its application in rare sugar synthesis [1].
A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase from Leuconostoc mesenteroides NRRL B-512F [2].

High impact information on 1,5-Anhydro-D-fructose

Recombinant 1,5-anhydro-d-fructose reductase (AFR) from Sinorhizobium morelense S-30.7.5 was crystallized in complex with the cofactor NADP(H) and its structure determined to 2.2 A resolution using selenomethionine SAD (refined R(work) and R(free) factors of 18.9 and 25.0%, respectively) [1].
N-linked oligosaccharide processing enzyme glucosidase II produces 1,5-anhydrofructose as a side product [3].
Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro [4].
The anhydrofructose pathway describes the degradation of glycogen and starch to 1,5-anhydro-D-fructose (1,5AnFru) and its further conversion to the enolone ascopyrone P (APP) via the transit intermediate ascopyrone M [5].
An unsaturated derivative, 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose (3), was obtained via regioselective elimination and acetylation of monohydrated 1,5-anhydro-D-fructose (1) in a single step reaction [6].

Biological context of 1,5-Anhydro-D-fructose

The antioxidant effects of 1,5-anhydro-D-fructose (1,5-AF), a unique anhydrohexulose, were studied in 1,1-diphenyl-2-picrylhydrazyl (DPPH) solution, in human cells along with lipid peroxidation of low-density lipoprotein (LDL) [4].
Basic toxicology and metabolism studies of 1,5-anhydro-D-fructose using bacteria, cultured mammalian cells, and rodents [7].
The phosphorylated forms of these compounds inhibited D-glucose phosphorylation by yeast hexokinase (Ki of phosphorylated 1,5-anhydro-D-fructose 0.11 mM; Ki of phosphorylated 1,5-anhydro-D-glucitol 0.38 mM) and rat brain hexokinase (Ki of phosphorylated 1,5-anhydro-D-fructose 0.07 mM; Ki of phosphorylated 1,5-anhydro-D-glucitol 0.04 mM) [8].

Associations of 1,5-Anhydro-D-fructose with other chemical compounds

Glucose 1-oxidase from Aspergillus niger was inhibited by 1,5-anhydro-D-fructose (Ki 6.6 mM) more effectively than 1,5-anhydro-D-glucitol (Ki 82.5 mM) [8].

Gene context of 1,5-Anhydro-D-fructose

1H- and 13C-NMR spectroscopic studies on unlabelled and labelled amylose (1-2H, 2-2H, 1-13C) as substrates indicated that the lyase cleaved the C-(1')-O(4) bond forming a double bond between C-1' and C-2', thus forming the enol form of 1,5-anhydro-D-fructose [9].

References

Crystal structure of NADP(H)-dependent 1,5-anhydro-D-fructose reductase from Sinorhizobium morelense at 2.2 A resolution: construction of a NADH-accepting mutant and its application in rare sugar synthesis. Dambe, T.R., Kühn, A.M., Brossette, T., Giffhorn, F., Scheidig, A.J. Biochemistry (2006) [Pubmed]
A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase from Leuconostoc mesenteroides NRRL B-512F. Richard, G., Yu, S., Monsan, P., Remaud-Simeon, M., Morel, S. Carbohydr. Res. (2005) [Pubmed]
N-linked oligosaccharide processing enzyme glucosidase II produces 1,5-anhydrofructose as a side product. Hirano, K., Ziak, M., Kamoshita, K., Sukenaga, Y., Kametani, S., Shiga, Y., Roth, J., Akanuma, H. Glycobiology (2000) [Pubmed]
Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro. Yamaji, K., Sarker, K.P., Maruyama, I., Hizukuri, S. Planta Med. (2002) [Pubmed]
Examination of 1,5-anhydro-D-fructose and the enolone ascopyrone P, metabolites of the anhydrofructose pathway of glycogen and starch degradation, for their possible application in fruits, vegetables, and beverages as antibrowning agents. Yuan, Y., Mo, S., Cao, R., Westh, B.C., Yu, S. J. Agric. Food Chem. (2005) [Pubmed]
Synthesis and co-polymerization of an unsaturated 1,5-anhydro-D-fructose derivative. Deppe, O., Glümer, A., Yu, S., Buchholz, K. Carbohydr. Res. (2004) [Pubmed]
Basic toxicology and metabolism studies of 1,5-anhydro-D-fructose using bacteria, cultured mammalian cells, and rodents. Yu, S., Mei, J., Ahrén, B. Food Chem. Toxicol. (2004) [Pubmed]
Effects of 1,5-anhydro-D-fructose on selected glucose-metabolizing enzymes. Taguchi, T., Haruna, M., Okuda, J. Biotechnol. Appl. Biochem. (1993) [Pubmed]
alpha-1,4-Glucan lyase, a new class of starch/glycogen degrading enzyme. III. Substrate specificity, mode of action, and cleavage mechanism. Yu, S., Ahmad, T., Kenne, L., Pedersén, M. Biochim. Biophys. Acta (1995) [Pubmed]

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