665
Views
2
CrossRef citations to date
0
Altmetric
Organic Chemistry

Syntheses and biological activities of deoxy-d-allose fatty acid ester analogs

, , &
Pages 676-681 | Received 08 Oct 2015, Accepted 17 Nov 2015, Published online: 28 Jan 2016

References

  • Izumori K. Bioproduction strategies for rare hexose sugars. Naturwissenschaften. 2002;89:120–124.10.1007/s00114-002-0297-z
  • Izumori K. Izumoring: a strategy for bioproduction of all hexoses. J. Biotechnol. 2006;124:717–722.10.1016/j.jbiotec.2006.04.016
  • Wanmeng M, Zhang W, Feng Y, et al. Recent advances on applications and biotechnological production of d-psicose. Appl. Microbiol. Biotechnol. 2012;94:1461–1467.
  • Hoshikawa H, Indo K, Mori T, et al. Enhancement of the radiation effects by d-allose in head and neck cancer cells. Cancer Lett. 2011;306:60–66.10.1016/j.canlet.2011.02.032
  • Granström TB, Izumori K, Leisola M. A rare sugar xylitol. part II: biotechnological production and future applications of xylitol. Appl. Microbiol. Biotechnol. 2007;74:273–276.10.1007/s00253-006-0760-4
  • Levin GV, Zehner LR, Saunders JP, et al. Sugar substitutes: their energy values, bulk characteristics and potential health benefits. Am. J. Clin. Nutr. 1995;62:1161S–1168S.
  • Hossain MA, Wakabayashi H, Goda F, et al. Effect of immunesuppressants FK506 and D-allose on allogenic orthotopic liver transplantation in rats. Transplant. Proc. 2000;32:2021–2023.10.1016/S0041-1345(00)01540-2
  • Yamaguchi F, Kamitori K, Sanada K, et al. Rare sugar d-allose enhances anti-tumor effect of 5-fluorouracil on the human hepato cellular carcinoma cell line HuH-7. J. Biosci. Bioengin. 2008;106:248–252.10.1263/jbb.106.248
  • Gao D, Kawai N, Tamiya T. The anti-inflammatory effects of d-allose contribute to attenuation of cerebral ischemia–reperfusion injury. Med. Hypotheses. 2011;76:911–913.10.1016/j.mehy.2011.03.007
  • Ishihara Y, Katayama K, Sakabe M, et al. Antioxidant properties of rare sugar D-allose: effects on mitochondrial reactiveoxygen species production in Neuro A cells. J. Biosci. Bioengin. 2011;112:638–642.10.1016/j.jbiosc.2011.08.005
  • Kimura S, Zhang G-X, Nishiyama A, et al. D-allose, an all-cis aldo-hexose, suppresses development of salt-induced hypertension in Dahl rats. J. Hypertens. 2005;23:1887–1894.10.1097/01.hjh.0000182523.29193.e3
  • Sui L, Nomura R, Dong Y, et al. Cryoprotective effects of d-allose on mammalian cells. Cryobiology. 2007;55:87–92.10.1016/j.cryobiol.2007.05.003
  • Hossain MA, Izuishi K, Maeta H. Protective effects of D-allose against ischemia reperfusion injury of the liver. J. Hepato-Biliary-Pancreatic Sci. 2003;10:218–225.10.1007/s00534-002-0785-8
  • Sui L, Dong Y, Watanabe Y, et al. The inhibitory effect and possible mechanisms of D-allose on cancer cell proliferation. Int. J. Oncol. 2005;27:907–912.
  • Murata A, Sekiya K, Watanabe Y, et al. A novel inhibitory effect of d-allose on production of reactive oxygen species from neutrophils. J. Biosci. Bioengin. 2003;96:89–91.10.1016/S1389-1723(03)90104-6
  • Kano A, Gomi K, Yamasaki-Kokudo Y, et al. A rare sugar, D-allose, confers resistance to rice bacterial blight with upregulation of defense-related genes in Oryza sativa. Phytopathology. 2010;100:85–90.10.1094/PHYTO-100-1-0085
  • Kato-Noguchi H, Takaoka T, Izumori K. Psicose inhibits the lettuce growth via a hexokinase-independent pathway. Physiol. Plant. 2005;125:293–298.10.1111/ppl.2005.125.issue-3
  • Afach G, Kawanami Y, Izumori K. Synthesis of D-allose fatty acid esters via lipase-catalyzed regioselective transesterification. Biosci. Biotechnol. Biochem. 2005;69:833–835.10.1271/bbb.69.833
  • Afach G, Kawanami Y, Kato-Noguchi H, et al. Practical production of 6-O-octanoyl-d-allose and its biological activity on plant growth. Biosci. Biotechnol. Biochem. 2006;70:2010–2012.10.1271/bbb.60150
  • Kobayashi M, Ueda M, Furumoto T, et al. Retarding activity of 6-O-acyl-D-allose against plant growth. Biosci. Biotechnol. Biochem. 2010;74:216–217.10.1271/bbb.90713
  • Fukumoto T, Kano A, Ohtani K, et al. Rare sugar D-allose suppresses gibberellin signaling through hexokinase-dependent pathway in Oryza sativa L. Planta. 2011;234:1083–1095.10.1007/s00425-011-1463-3
  • Chowdhury MTI, Naito M, Yanagita RC, et al. Synthesis of 6-O-decanoyl-d-gulose and 6-O-decanoyl-D-gulose and evaluation of their biological activity on plant growth. Plant Growth Regul. 2015;75:707–713.10.1007/s10725-014-9972-2
  • Haga M, Tejima S. Synthesis of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-d-ribo-hex-1-enitol and 2,3,4,6-tetra-O-acetyl-1,5-anhydro-d-ribo-hex-1-enitol. Carbohydr. Res. 1974;34:214–218.10.1016/S0008-6215(00)80388-2
  • Morris WJ, Shair MD. Stereoselective synthesis of 2-deoxy-ß-glycosides using anomeric O-alkylation/arylation. Org. Lett. 2009;11:9–12.10.1021/ol8022006
  • Guthrie RD, Irvine RW. A facile synthesis of D-allal and its derivatives. Carbohydr. Res. 1979;72:285–288.10.1016/S0008-6215(00)83951-8
  • Fujii T. Biosurfactants. J. Jpn. Oil Chem. Soc. 1996;45:1013–1021.10.5650/jos1996.45.1013
  • Ogino K. Research and development of novel surfactants. J. Jpn. Oil Chem. Soc. 1996;45:921–932.10.5650/jos1996.45.921
  • Crozier A, Kamiya Y, Bishop G, et al. Biosynthesis of hormones and elicitor molecules. In: Buchanan B, Guissem W, Jones R, editors. Biochemistry and molecular biology of plants. Rockville, Maryland: American Society of Plant Physiologist; 2000. p. 850–929.
  • Rademacher W. Growth retardants effects on gibberellins biosynthesis and other metabolic pathways. Annu. Rev. Plant Physiol. Plant Mol. Biol. 2000;51:501–531.10.1146/annurev.arplant.51.1.501
  • Robins MJ, Nowak I, Wnuk SF, et al. Deoxygenative [1,2]-hydride shift rearrangements in nucleoside and sugar chemistry: analog with the [1,2]-electron shift in the deoxygenation of ribonucleotide reductases. J. Org. Chem. 2007;72:8216–8221.10.1021/jo071102b

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.