[(2R,3S,5R)-5-(6,7-dimethyl-2-oxo-4-sulfanylidenepteridin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate | 183279-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: [(2R,3S,5R)-5-(6,7-dimethyl-2-oxo-4-sulfanylidenepteridin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 183279-00-7
• 化学式: C₂₉H₂₈N₄O₆S
• 分子量: 560.631
• InChiKey: FINJFVGCXCEDMW-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-5-(6,7-dimethyl-2-oxo-4-sulfanylidenepteridin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate 在 氨 作用下， 生成 [6,7-Dimethyl-2-oxo-1-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pteridin-4-yl]-carbamic acid 2-(4-nitro-phenyl)-ethyl ester
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188
• 作为产物：
  描述：

  1-[O3,O5-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-6,7-dimethyl-1H-pteridine-2,4-dione 在 tetraphosphorus decasulfide 作用下， 以75%的产率得到[(2R,3S,5R)-5-(6,7-dimethyl-2-oxo-4-sulfanylidenepteridin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188

文献信息

• Rosler, Angelika; Pfleiderer, Wolfgang, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S230 - S233
  作者：Rosler, Angelika、Pfleiderer, Wolfgang

  DOI：——

  日期：——
• PTERIDINE NUCLEOTIDE ANALOGS AS FLUORESCENT DNA PROBES
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by the SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0759927A1

  公开（公告）日：1997-03-05
• US5525711A
  申请人：——

  公开号：US5525711A

  公开（公告）日：1996-06-11
• US5612468A
  申请人：——

  公开号：US5612468A

  公开（公告）日：1997-03-18
• [EN] PTERIDINE NUCLEOTIDE ANALOGS AS FLUORESCENT DNA PROBES<br/>[FR] ANALOGUES DE NUCLEOTIDES DE PTERIDINE SOUS FORME D'ECHANTILLONS D'ADN FLUORESCENTS
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1995031469A1

  公开（公告）日：1995-11-23

  (EN) The invention provides novel pteridine nucleotide which are highly fluorescent under physiological conditions and which may be used in the chemical synthesis of fluorescent oligonucleotides. The invention further provides for fluorescent oligonucleotides comprising one or more pteridine nucleotides. In addition the invention provides for pteridine nucleotide triphosphates which may be used as the constituent monomers in DNA amplification procedures.(FR) L'invention concerne de nouveaux nucléotides de ptéridine fortement fluorescents dans des conditions physiologiques et pouvant être utilisés dans la synthèse chimique d'oligonucléotides fluorescents. L'invention concerne également des oligonucléotides fluorescents comprenant un ou plusieurs nucléotides de ptéridine. L'invention concerne en outre des triphosphates de nucléotide de ptéridine pouvant être utilisés en tant que monomères constitutifs dans les procédés d'amplification d'ADN.