An Improved Phosphoramidite Approach for the Chemical Synthesis of 3’,5’-Cyclic Diguanylic Acid
作者: Andrzej GrajkowskiMayumi TakahashiTomasz KaczyńskiSuresh C. SrivastavaSerge L. Beaucage
作者单位: 1Laboratory of Biological Chemistry, Division of Biotechnology Review and Research IV, Center for Drug Evaluation and Research, Food and Drug Administration, 10903 New Hampshire Avenue, Silver Spring, Maryland 20933, United States
2ChemGenes Corporation, 33 Industrial Way, Wilmington, Massachusetts 01887, United States
刊名: Tetrahedron Letters, 2019
来源数据库: Elsevier Journal
DOI: 10.1016/j.tetlet.2019.01.006
关键词: 5’-O-formyl esterChemoselective cleavageCyclocondensation reactionPhosphoramidite intermediatesPhosphoramidite/H-phosphonate intermediates
原始语种摘要: Abstract(#br)3’,5’-Cyclic diguanylic acid (c-di-GMP) plays important roles as a signaling and effector molecule in prokaryotes as well as inducing innate and adaptive immune responses in mammalian cells through activation of cell death pathways. An improved phosphoramidite method for the synthesis of c-di-GMP is reported herein. The method is based on the use of an unprecedented 5’- O -formyl ester, which can efficiently and chemoselectively be cleaved from a dinucleotide phosphoramidite intermediate to permit a 1 H -tetrazole-mediated cyclocondensation reaction leading to a fully protected c-di-GMP product in a yield of 78%. The native c-di-GMP is isolated in an overall yield of 36% based on the commercial ribonucleoside used as starting material.
全文获取路径: Elsevier  (合作)
影响因子:2.397 (2012)

  • phosphonate 膦酸盐
  • formyl 甲酰
  • reaction 反酌
  • ester 
  • cleavage 解理