Chemical Modification of Lactose. IX. Synthesis of O-β-D-Galactopyranosyl-(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose (6'-Galactosyllactose)
スポンサーリンク
概要
- 論文の詳細を見る
The title trisaccharide was synthesized from 1,6-anhydro-β-lactose. Condensation of 2,2', 3,3'-tetra-O-acetyl-1,6-anhydro-β-lactose and 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide by a modified Koenigs-Knorr reaction followed by acetylation gave acetylated 1,6-anhydro-β-trisaccharide (3) in 62% yield. The β-configuration for the new galactosidic linkage was obtained from the value of the molecular rotation of 3. Deacetylation of 3 afforded 1,6-anhydro-β-trisaccharide (4). The structure was determined by a gas chromatographic (GC) analysis and a gas chromatography-mass spectrometry of acid hydrolysate of permethylated 4. Acetolysis of 3 under mild condition proceeded cleavage of the 1,6-anhydro-β-ring and afforded acetylated trisaccharide contaminated with acetylated galactose and lactose. From the acetolysis mixture, the title trisaccharide was isolated via acetylated β-trisaccharide followed by deacetylation. The structure was determined by GC analysis of the partial methylated alditol acetates obtained from the hydrolysate of permethylated, borohydride reduced trisaccharide.
- 社団法人日本薬学会の論文
- 1978-07-25
著者
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石原 英子
名古屋市立大学
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手島 節三
名古屋市立大学薬学部
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石原 英子
Faculty of Pharmaceutical Sciences, Nagoya City University
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手島 節三
Faculty of Pharmaceutical Sciences, Nagoya City University
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鄭 大基
Faculty of Pharmaceutical Sciences, Nagoya City University
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手島 節三
Faculty Of Pharmaceutical Sciences Nagoya City University
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鄭 大基
Faculty Of Pharmaceutical Sciences Nagoya City University
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