title: Identification of rare 6-deoxy-D-altrose from an edible mushroom (Lactarius lividatus).
abstract: 6-Deoxy-L-altrose is well known as a constituent sugar moiety of lipopolysaccharides in Gram-negative bacteria. However, its isomer, 6-deoxy-D-altrose, is little known. Identification of 6-deoxy-D-altrose isolated from a polysaccharide extracted from an edible mushroom (Lactarius lividatus), its comparison with chemically synthesized 6-deoxy-D-altrose using (1)H and (13)C NMR including COSY, HMQC spectroscopy, and investigation of its specific optical rotation were all conducted in this study. The 6-deoxy-hexose isolated from acid hydrolysate of the polysaccharide extracted from L. lividatus was involved in four anomeric isomers (α-pyranose and β-pyranose, and α-furanose and β-furanose), as was chemically synthesized 6-deoxy-d-altrose in an aqueous solution because of mutarotation. Almost all signals of 1D ((1)H NMR and (13)C NMR) and 2D (COSY and HMQC)-NMR spectra agreed with those of the authentic 6-deoxy-D-altrose. The specific optical rotation [α](589) of 6-deoxy-sugar showed a value of +18.2°, which was in agreement with that of authentic 6-deoxy-D-altrose. Consequently, 6-deoxy-hexose was identified as the 6-deoxy-D-altrose. This work is the first complete identification of 6-deoxy-D-altrose in a natural environment.
authors.affiliation: Department of Subtropical Bioscience and Biotechnology, University of the Ryukyus, Nishihara, Okinawa, Japan. tako@agr.u-ryukyu.ac.jp
authors.forename: Masakuni
authors.initials: M
authors.lastname: Tako
authors.forename: Yahiko
authors.initials: Y
authors.lastname: Dobashi
authors.forename: Yukihiro
authors.initials: Y
authors.lastname: Tamaki
authors.forename: Teruko
authors.initials: T
authors.lastname: Konishi
authors.forename: Masashi
authors.initials: M
authors.lastname: Yamada
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D003837:Deoxy Sugars / Q000032:analysis* / Q000737:chemistry; D006601:Hexoses / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011134:Polysaccharides / Q000737:chemistry
chemical_list: D003837:Deoxy Sugars; D006601:Hexoses; D011134:Polysaccharides; C053979:6-deoxyaltrose