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Georganics

L-Xylose – preparation and application

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L-Xylose [609-06-3] is a rare monosaccharide of the aldopentose type first isolated from wood, and named for it (ancient greek: ξύλον, xylon, « wood »). It is a white crystalline solid with the melting point of 144-145 °C.[1]

L-Xylose can be prepared by chemical route from D-gluconolactone [2] or from D-sorbitol.[3],[4] Enzymatic isomerization of the ketosugar L-xylulose to L-xylose has been presented as an alternative for low yields chemical synthesis. The starting material, L-xylulose can be produced by oxidation of the relatively cheap polyol, xylitol, using natural bacterial isolates as whole cell catalysts.[5]

Application of Furoin:

L-xylose is used in organic synthesis as a chiral building block. It was used for the synthesis of L-ascorbic acid.[6]  Novel L-xylose derivatives have recently been reported to act as inhibitors of urinary glucose reabsorption, which suggests that they may find use in diabetes treatment.[7] Polyhydroxypyrrolidines derived from l-xylose have shown antitumor and anti-HIV properties and act as potent α- and β-glucosidase inhibitors, which also is of relevance for the development of diabetes drugs.[8]

Product categorization (Chemical groups):

Main category:

Second level:

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[1] T. G. Bonner, E. J. Bourne, S. E. Harwood, D. Lewis J. Chem. Soc. 1965, 121. doi:10.1039/JR9650000121
[2] W. B. Yang, S. S. Patil, C. H. Tsai, C. H. Lin, J. M. Fang Tetrahedron 2002, 58 (2), 253. doi:10.1016/S0040-4020(01)01146-2
[3] E. Dimant, M. Banay J. Org. Chem. 1960, 25 (3), 475. doi:10.1021/jo01073a621
[4] R. C. Hockett Production of l-xylose 1952, HEINZ M WUEST, US2584129A.
[5] A. Usvalampi, O. Turunen, J. Valjakka, O. Pastinen, M. Leisola, A. Nyyssölä Enzyme. Microb. Technol. 2012, 50 (1), 71. doi:10.1016/j.enzmictec.2011.09.009
[6] L. L. Salomon, J. J. Burns, C. G. King J. Am. Chem. Soc. 1952, 74 (20), 5161. doi:10.1021/ja01140a051
[7] N. C. Goodwin, R. Mabon, B. A. Harrison, M. K. Shadoan, Z. Y. Almstead, Y. Xie, J. Healy, L. M. Buhring, C. M. DaCosta, J. Bardenhagen, F. Mseeh, Q. Liu, A. Nouraldeen, A. G. E. Wilson, S. D. Kimball, D. R. Powell, D. B. Rawlins J. Med. Chem. 2009, 52 (20), 6201. doi:10.1021/jm900951n
[8] J. B. Behr, G. Guillerm Tetrahedron Lett. 2007, 48 (13), 2369. doi:10.1016/j.tetlet.2007.01.125