31 オリゴ糖配糖体の選択的開裂法の研究 : グルクロナイド結合の開裂

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概要

• 論文の詳細を見る

• In search of a new selective cleavage method of certain glycoside linkage in oligosaccharide-glycoside, three new methods for selective cleavage of a glucuronide linkage in saponin have been developed. I. Photolysis It has been found that ultraviolet irradiation is a convenient procedure for degradation of some oleanane-type saponins resulting in liberation of their genuine sapogenols (Table I). Studies on the structure requirement for the ready photolysis have shown that a glucuronic acid moiety directly connected to the sapogenol is an essential constituent in the carbohydrate portion (cf. glucuronide-saponin). II. Pb(OAc)_4 Degradation Pb(OAc)_4 oxidation followed by a brief treatment with alkali of permethylated derivative of glucuronide-saponin possessing free carboxyl function readily affords methylated sapogenol and methylated carbohydrate ingredients. For example, 23 is decomposed to 21 via 24 and 25 almost quantitatively, and 27 to 29, 30, 31, 32, and 33 via 28 in excellent yields. III. Ac_2O-Pyridine Degradation On heating in Ac_2O-pyridine (2:1) mixture, glucuronide-saponin possessing carbohydrate chains at C-2 and C-4 of its glucuronide moiety is decomposed to acetylated sapogenol and acetylated carbohydrate derivatives. To accomplish the degradation, both Ac_2O and pyridine are indispensable. The above described three methods seem to be useful in the structure study of polysaccharide containing the glucuronide linkage and the other kinds of uronide linkage.

• 天然有機化合物討論会の論文
• 1975-10-01

著者

• 北川 勲

  阪大薬

• 池西 裕二

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 吉岡 一郎

  阪大薬学部

• 任 光植

  Faculty Of Pharmaceutical Sciences Osaka University:(present Address)college Of Pharmacy Busan Natio

• 吉川 雅之

  阪大薬

• 池西 裕二

  阪大薬

• 任 光植

  阪大薬

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