期刊文献+

海洋糖脂Erylusamine B四糖片段的合成研究

Synthesis of tetrasaccharide fragment of marine glycolipid Erylusamine B
原文传递
导出
摘要 目的 对海洋糖脂Erylusamine B的四糖片段进行合成研究,旨在为Erylusamine B的全合成及构效关系研究奠定基础。方法 以D-木糖为原料,通过7步反应以25.1%的产率制备了2-OH裸露的木糖受体6,经6步反应以55.3%的产率制备了4-OH裸露的木糖受体11;以全乙酰化的阿拉伯糖硫苷为原料,通过两步反应以87%的产率合成了三氯乙酰亚胺酯供体13,通过4步反应以59%的产率合成了硫苷供体16;供体13和木糖受体11进行糖苷化反应合成Ara-α-(1→4)-Xyl二糖17;硫苷供体16和木糖受体6经糖苷化反应合成Ara-α-(1→2)-Xyl二糖19;二糖供体17和二糖受体19经NIS/TMSOTf催化顺利合成四糖20。结果 通过[2+2]汇聚式合成策略以83%的糖苷化产率得到Ara-α-(1→4)-Xyl-β-(1→3)-[Ara-α-(1→2)]-Xyl四糖产物(20),为海洋糖脂Erylusamine B的合成提供物质基础和技术手段。 Objective The tetrasaccharide fragment of marine glycolipid Erylusamine B was synthesized for the total synthesis of Erylusamine B and its biological activity in the future.Methods Xylose receptors 6 and 11 were synthesized from D-xylose with overall yields of 25.1% and 55.3%,respectively;arabinose trichloroacetimidate donor 13 and thiolglycoside donor 16 were synthesized from p-Tolyl-2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside 12 with 87% and 59% yields,respectively.Donor 13 was reacted with xylose acceptor 11 to afford the Ara-α-(1→4)-Xyl disaccharide 17.Thiolglycoside donor 16 coupled with xylose acceptor 6 to afford the Ara-α-(1→2)-Xyl disaccharide 19.Glycosylation of disaccharide donor 17 with acceptor 19 gave the tetrasaccharide fragment under the action of NIS and TMSOTf.Results Ara-α-(1→4)-Xyl-β-(1→3)-[Ara-α-(1→2)]-Xyl tetrasaccharide fragment 20 was obtained in 83% yield by a [2+2] convergent strategy,providing the material basis and technology for the synthesis of the marine glycolipid Erylusamine B.
作者 李发荣 吕昌仑 曹爽 李春霞 LI Farong;LYU Changlun;CAO Shuang;LI Chunxia(Key Laboratory of Marine Drugs,Ministry of Education,Shandong Key Laboratory of Glycoscience and Glycotechnology,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China;Marine Biomedical Research Institute of Qingdao,Qingdao 266071,China)
出处 《中国海洋药物》 CAS CSCD 2024年第5期17-27,共11页 Chinese Journal of Marine Drugs
基金 国家自然科学基金项目(U21A20297) 山东省重点研发计划重大科技创新工程(2021ZDSYS22)资助。
关键词 糖脂 Erylusamine B 糖苷化 四糖 glycolipid Erylusamine B glycosylation tetrasaccharide
  • 相关文献

参考文献3

二级参考文献74

  • 1Woo P,,Wilkinson N,Kishimoto T,et al.Open label phase II trial of single,ascending doses of MRA in Cau-casian children with severe systemic juvenile idiopathic arthritis:proof of principle of the efficacy of IL-6receptor blockade in this type of arthritis and demonstration of prolonged clini. Arthritis Research and Therapy . 2005
  • 2Axmann R,Bnhm C,Krnnke G,et al.Inhibition of in-terleukin-6receptor directly blocks osteoclast formation in vitro and in vivo. Arthritis and Rheumatism . 2009
  • 3Okiyama N,Sugihara T,Iwakura Y,et al.Therapeutic effects of interleukin-6blockade in a murine model of polymyositis that does not require interleukin-17A. Arthritis and Rheumatism . 2009
  • 4Hirano T.Interleukin6and its receptor:ten years later. International Reviews of Immunology . 2004
  • 5Plushner SL.Tocilizumab:an Interleukin-6receptor in-hibitor for the treatment of rheumatoid arthritis. Annals of Pharmacotherapy . 2008
  • 6Chen X,Das R,Komorowski R,et al.Blockade of in-terleukin-6signaling augments regulatory T-cell reconstitu-tion and attenuates the severity of graft-versus-host disease. Blood . 2009
  • 7Maini RN,Taylor PC,Smolen J,et al.Double-blind randomized controlled clinical trial of the interleukin-6re-ceptor antagonist,tocilizumab,in European patients with rheumatoid arthritis who had an incomplete response to methotrexate. Arthritis and Rheumatism . 2006
  • 8Hirano T,Yasukawa K,Harada H,et al.Complementary DNA for a novel human interleukin (BSF-2) that induces B lymphocytes to produce immunoglobulin. Nature . 1986
  • 9Ulich TR,Yin S,Guo K,et al.Intratracheal injection of endotoxin and cytokines. II. Interleukin-6 and transforming growth factor beta inhibit acute inflammation. American Journal of Pathology . 1991
  • 10Tamura T,Udagawa N,Takahashi N,et al.Soluble interleukin-6 receptor triggers osteoclast formation by interleukin-6. Proceedings of the National Academy of Sciences of the United States of America . 1993

共引文献21

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部