Synthesis of Alkyl Oligosaccharide by Ring-Opening Polymerization of Anhydro Sugars

脱水糖开环聚合合成烷基低聚糖

• 批准号: 04453112
• 负责人: URYU Toshiyuki
• 金额: $ 4.42万
• 依托单位: University of Tokyo
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (B)
• 财政年份: 1992
• 资助国家: 日本
• 起止时间: 1992 至 1993
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-04453112/
• 关键词: Alkyl oligosaccharide; Oligo-ribose; Ring-opening polymerization; Anhydro sugar; Sulfated alkyl oligo-ribose; Anti-HIV-activity; Glycosidation; Poly-deoxy-ribose; グリコシレーション; ルイス酸触媒; 硫酸化; 高分解能NMR; 抗エイズウイルス作用

In our laboratory, following the synthesis of highly anti-HIV (human immunodeficiency virus) active sulfated polysaccharides, sulfated alkyl oligosaccharides with potent anti-HIV activity were prepared. The sulfated alkyl oligosaccharide has such a structure that a long alkyl group is attached to the reducing end of the sulfated oligosaccharide. In this study, modifying the synthetic method of high molecular weight stereoregular polysaccharides, medium molecular weight polysaccharides, i.e., polyriboses, were prepared by selective cationic ring-opening polymerization of a 1,4-anhydro-ribose derivative. The acetylated polyribose, i.e., acetylated (1->5)-alpha-ribofuranan, was reacted with octadecyl alcohol by stannic chloride catalyst to afford acetylated alkyl polyribose with medium molecular weight. After deacetylation, OH-free alkyl oligo-riboses were sulfated into sulfated alkyl oligo-riboses with anti-HIV activity. In addition, a new 1,4-anhydro-deoxy-ribose monomer was synthesized and polymerized into a stereoregular poly-deoxy-ribose. This deoxy-ribose derivative has a potential to be used for the synthesis of another alkyl oligosaccharide.

本实验室在合成高抗hiv（人类免疫缺陷病毒）活性磺化多糖的基础上，制备了具有强抗hiv活性的磺化烷基低聚糖。硫酸化烷基低聚糖具有这样的结构，即长烷基连接在硫酸化低聚糖的还原端。本研究改进了高分子量体正多糖的合成方法，采用1,4-无氢核糖衍生物的阳离子开环选择性聚合法制备了中等分子量的多糖，即聚核糖。在氯化锡催化剂下，将乙酰化的(1- bbb50)- α -核呋喃与十八烷基醇反应，得到中等分子量的乙酰化烷基核糖。脱乙酰化后，无oh烷基低聚核糖被硫酸化成具有抗hiv活性的硫酸化烷基低聚核糖。此外，还合成了一种新的1,4-无氢脱氧核糖单体，并将其聚合成立体规则的多脱氧核糖。该脱氧核糖衍生物具有用于合成另一烷基低聚糖的潜力。

项目成果

T.Uryu,N.Ikushima,K.Katsuraya,T.Shoji,N.Takahashi,T.Yoshida,K.Kanno,H.Nakashima,N.Yamamoto: "Sulfated Alkyl Oligosaccharides with Potent Inhibitory Effects on Human Immunodeficiency Virus Infection" Biochem.Pharm.43. 2385-2392 (1992)

T.Uryu、N.Ikushima、K.Katsuraya、T.Shoji、N.Takahashi、T.Yoshida、K.Kanno、H.Nakashima、N.Yamamoto：“对人类免疫缺陷病毒感染具有有效抑制作用的硫酸化烷基寡糖”

T.Uryu, N.Ikushima, K.Katsuraya, T.Shoji, N.Takahashi, T.Yoshida, K.Kanno, H.Nakashima and N.Yamamoto: "Sulfated Alkyl Oligosaccharides with Potent Inhibitory Effects on Human Immunodeficiency Virus Infection" Biochem.Pharm. 43. 2385-2392 (1992)

T.Uryu、N.Ikushima、K.Katsuraya、T.Shoji、N.Takahashi、T.Yoshida、K.Kanno、H.Nakashima 和 N.Yamamoto：“对人类免疫缺陷病毒感染具有有效抑制作用的硫酸化烷基寡糖”

T.Yoshida,Y.Katayama,S.Inoue,and T.Uryu: "Synthesis of Branched Ribofuranans and Their Sulfates with Potent Anti-AIDS Virus Activity by Selective Ring-Opening Copolymerization of 1,4-Anhydro-α" Maclomolecules. 25. 4051-4057 (1992)

T. Yoshida、Y. Katayama、S. Inoue 和 T. Uryu：“通过 1,4-AnHydro-α 选择性开环共聚合成具有有效抗艾滋病病毒活性的支链呋喃核糖及其硫酸盐”25。 .4051-4057 (1992)

T.Yoshida,Y.Katayama,S.Inoue,and T.Uryu: "Synthesis of Branched Ribofuranans and Their Sulfates with Potent Anti-AIDS Virus Activity by Selective Ring-Opening Copolymerization of 1,4-Anhydro-α" Maclomolecules. 25. 4051-4057 (1992)"-D-ribopyranose Derivati

T. Yoshida、Y. Katayama、S. Inoue 和 T. Uryu：“通过 1,4-AnHydro-α 选择性开环共聚合成具有有效抗艾滋病病毒活性的支链呋喃核糖及其硫酸盐”25。 4051-4057 (1992)"-D-吡喃核糖衍生物

T.Uryu: "“Carbohydrate and Carbohydrate Polymers" (分担)" ATL Press, 15 (1993)

T.Uryu：““碳水化合物和碳水化合物聚合物”（分享）”ATL Press，15（1993）