Chemical Modification of Lactose. IV. Syntheses of Disaccharide Derivatives Predominantly Modified at the C-6 Position in Lactose

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概要

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• The title compounds are required for the substrate specificity study on β-D-galactosidase (EC 3.2.1.23). Starting from 1,2,3,2', 3', 4', 6'-hepta-O-acetyl-β-lactose, 4-O-β-D-galactopyranosyl-α-D-glucuronic acid, 6-O-methyl-α-lactose, methyl 3,6-anhydro-β-lactoside, and 6-deoxy-α-lactose were synthesized. 1,2,3-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -β-D-xylo-hex-5-eno-pyranose (13) was also prepared by elimination of hydrogen iodide with silver fluoride in dry pyridine from 1,2,3,2', 3', 4', 6'-hepta-O-acetyl-6-deoxy-6-iodo-β-lactose. In catalytic hydrogenation of 13,regardless of the catalyst, a stereospecific hydrogenation proceeded in such a way that the 6-deoxy-L-ido isomer, 1,2,3-tri-O-acetyl-4-O- (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -6-deoxy-α-L-idopyranose (14), was overwhelmingly predominant than the corresponding 6-deoxy-D-gluco isomer, 1,2,3-tri-O-acetyl-4-O- (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -6-deoxy-β-D-glucopyranose. The result was the reverse with that reported in unsaturated monosaccharide series. Deacetylation of 14 afforded 4-O-β-D-galactopyranosyl-6-deoxy-L-idopyranose as a hygroscopic powder.

• 社団法人日本薬学会の論文
• 1974-02-25

著者

• 手島 節三

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 千葉 拓

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 羽賀 正信

  Faculty of Pharmaceutical Sciences, School of Medicine, Hokkaido University, Nishi-5-chome, Kita-12-

• 手島 節三

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 羽賀 正信

  Faculty Of Pharmaceutical Sciences Health Sciences University Of Hokkaido

• 千葉 拓

  名古屋市立大学薬学部

関連論文

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• Chemical Modification of Lactose. XIII. Synthesis of Lacto-N-tetraose
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