期刊文献+

Chemoenzymatic synthesis of α2–3-sialylated carbohydrate epitopes

Chemoenzymatic synthesis of α2–3-sialylated carbohydrate epitopes
原文传递
导出
摘要 Sialic acids are common terminal carbohydrates on cell surface.Together with internal carbohydrate structures,they play important roles in many physiological and pathological processes.In order to obtain α2–3-sialylated oligosaccharides,a highly efficient one-pot three-enzyme synthetic approach was applied.The P.multocida α2–3-sialyltransferase (PmST1) involved in the synthesis was a multifunctional enzyme with extremely flexible donor and acceptor substrate specificities.Sialyltransferase acceptors,including type 1 structure (Galβ1–3GlcNAcβProN3),type 2 structures (Galβ1–4GlcNAcβProN3 and 6-sulfo-Galβ1– 4GlcNAcβProN3),type 4 structure (Galβ1–3GalNAcβProN3),type 3 or core 1 structure (Galβ1–3GalNAcβProN3) and human milk oligoscaccharide or lipooligosaccharide lacto-N-tetraose (LNT) (Galβ1–3GlcNAcβ1–3Galβ1–4GlcβProN3),were chemically synthesized.They were then used in one-pot three-enzyme reactions with sialic acid precursor ManNAc or ManNGc,to synthesize a library of naturally occurring β2–3-linked sialosides with different internal sugar structures.The sialylated oligosaccharides obtained are valuable probes for their biological studies. Sialic acids are common terminal carbohydrates on cell surface.Together with internal carbohydrate structures,they play important roles in many physiological and pathological processes.In order to obtain α2–3-sialylated oligosaccharides,a highly efficient one-pot three-enzyme synthetic approach was applied.The P.multocida α2–3-sialyltransferase (PmST1) involved in the synthesis was a multifunctional enzyme with extremely flexible donor and acceptor substrate specificities.Sialyltransferase acceptors,including type 1 structure (Galβ1–3GlcNAcβProN3),type 2 structures (Galβ1–4GlcNAcβProN3 and 6-sulfo-Galβ1– 4GlcNAcβProN3),type 4 structure (Galβ1–3GalNAcβProN3),type 3 or core 1 structure (Galβ1–3GalNAcβProN3) and human milk oligoscaccharide or lipooligosaccharide lacto-N-tetraose (LNT) (Galβ1–3GlcNAcβ1–3Galβ1–4GlcβProN3),were chemically synthesized.They were then used in one-pot three-enzyme reactions with sialic acid precursor ManNAc or ManNGc,to synthesize a library of naturally occurring β2–3-linked sialosides with different internal sugar structures.The sialylated oligosaccharides obtained are valuable probes for their biological studies.
出处 《Science China Chemistry》 SCIE EI CAS 2011年第1期117-128,共12页 中国科学(化学英文版)
基金 supported by NIH grants R01GM076360 and U01CA128442
关键词 CARBOHYDRATE chemoenzymatic synthesis sialic acid SIALYLATION SIALYLTRANSFERASE 唾液酸酶 酶法合成 化学合成 低聚糖 酸化 化合物结构 碳水化合物 抗原
  • 相关文献

参考文献40

  • 1E. M. Rapoport,G. V. Pazynina,M. A. Sablina,P. R. Crocker,N. V. Bovin.Probing sialic acid binding Ig-like lectins (siglecs) with sulfated oligosaccharides[J]. Biochemistry (Moscow) . 2006 (5)
  • 2R. J. Russell,D. J. Stevens,L. F. Haire,S. J. Gamblin,J. J. Skehel.Avian and human receptor binding by hemagglutinins of influenza A viruses[J]. Glycoconjugate Journal . 2006 (1-2)
  • 3Noboru Tomiya,Someet Narang,Yuan C. Lee,Michael J. Betenbaugh.Comparing N-glycan processing in mammalian cell lines to native and engineered lepidopteran insect cell lines[J]. Glycoconjugate Journal . 2004 (6)
  • 4Roland Schauer.Achievements and challenges of sialic acid research[J]. Glycoconjugate Journal . 2000 (7-9)
  • 5Essentials of Glycobiology. . 2008
  • 6Seymour JL,Costello CE,Zaia J.The influence of sialylation on glycan negative ion dissociation and energetics. Journal of the American Society for Mass Spectrometry . 2006
  • 7Chandrasekaran A,Srinivasan A,Raman R,Viswanathan K,Raguram S,Tumpey TM,Sasisekharan V,Sasisekharan R.Glycan topology determines human adaptation of avian H5N1 virus hemagglutinin. Nature Biotechnology . 2008
  • 8Gamblin SJ,Haire LF,Russell RJ,Stevens DJ,Xiao B,Ha Y,Vasisht N,Steinhauer DA,Daniels RS,Elliot A,Wiley DC,Skehel JJ.The structure and receptor binding properties of the 1918 influenza hemagglutinin. Science . 2004
  • 9Crocker PR,Varki A.Siglecs in the immune system. Immunology . 2001
  • 10Campanero-Rhodes MA,Childs RA,Kiso M,Komba S,Le Narvor C,Warren J,Otto D,Crocker PR,Feizi T.Carbohydrate microarrays reveal sulphation as a modulator of siglec binding. Biochemical and Biophysical Research Communications . 2006

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