Assignment of the absolute configuration of 3,6-anhydrogalactose derivatives via diastereomeric glycosylation of threose derivatives obtained by periodate Oxidation.: University of the Ryukyus Repository


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University of the Ryukyus Repository >
Faculty of Agriculture >
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The Science Bulletin of the Faculty of Agriculture. University of the Ryukyus >
No.64 (2017/12) >

Title	:	Assignment of the absolute configuration of 3,6-anhydrogalactose derivatives via diastereomeric glycosylation of threose derivatives obtained by periodate Oxidation.
Title alternative	:	過ヨウ素酸酸化によるトレオース誘導体のグリコシドジアステレオマーを経由した3,6-アンヒドロガラクトースの絶対配置の帰属
Authors	:	Takano, Ryo Tohma, Yurina
Authors alternative	:	高野, 良當間, 優里菜
Issue Date	:	28-Dec-2017
Abstract	:	In order to assign the absolute configuration of 3,6-anhydrogalactose and its 2-Omethylether, their dimethylacetals were subjected to periodate oxidation to yield 3-O-(2-hydroxy-methyl) threose dimethylacetal derivatives, which were further derivatized to the diastereomeric glycosides with (R)- or (S)-2-octanol. Their TMS derivatives were completely resolved by gas-liquid chromatography. Complication in the chromatogram due to contaminants or by-products, when this procedure was applied to total methanolysate of the red algal galactans, was overcome by monitoring the fragment ion of m/z = 116 in the mass spectra using selected ion monitor (SIM)chromatogram using GC-MS. 紅藻の多糖の主要成分である3,6-アンヒドロガラクトースの絶対配置を帰属するため、3,6-アンヒドロガラクトースジメチルアセタールを過ヨウ素酸酸化して3-O-(2-ヒドロキシメチル)トレオースジメチルアセタールに変換し、さらにこのものを(R)-または(S)-2-オクタノールとのジアステレオマーのグリコシドに導いた。これらをTMS 誘導体としてGLC 分析したところ、両ジアステレオマーは完全に分離された。また、3,6-アンヒドロ-2-O-メチルガラクトースも同様に分離することができた。この方法を紅藻多糖の完全メタノリシス化物に適用すると、クロマトグラムは夾雑物または副生成物により複雑化するが、GC-MS を用い、m/z = 116 のフラグメントイオンを用いたSIM クロマトグラフィーを適用することにより解決された。
Type Local	:	紀要論文
ISSN	:	0370-4246
Publisher	:	琉球大学農学部
URI	:	http://hdl.handle.net/20.500.12000/40910
Citation	:	琉球大学農学部学術報告 = THE SCIENCE BULLETIN OF THE FACULTY OF AGRICULTURE UNIVERSITY OF THE RYUKYUS no.64 p.33 -39
Appears in Collections	:	No.64 (2017/12)

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