1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol | 383859-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol
• 英文别名: 1,5-anhydro-6-O-monomethoxytrityl-2-(N⁶-benzoyl-adenin-9-yl)-2,3-dideoxy-D-glucitol
• CAS: 383859-49-2
• 化学式: C₃₈H₃₅N₅O₅
• 分子量: 641.726
• InChiKey: XGHLCASUCRXRDR-NGYIUDBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  48.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  120.62
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到1′,5′-anhydro-2′-(N(6)-benzoyladenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-4′-O-[N,N-diisopropyl(2-cyanoethyl) phosphoramidite]-D-ribohexitol
  参考文献：
  名称：

  1′,5′-Anhydro-l-ribo-hexitol Adenine Nucleic Acids (α-l-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World

  摘要：

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.

  DOI：

  10.1021/acs.joc.5b00406
• 作为产物：
  描述：

  (2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 三甲基氯硅烷 、 palladium 10% on activated carbon 、 mercury(II) diacetate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 100.0 ℃ 、137.9 kPa 条件下， 反应 113.0h， 生成 1′,5′-anhydro-2′-(N(6)-benzoyl-adenin-9-yl)-2′,3′-dideoxy-6′-O-monomethoxytrityl-D-ribohexitol
  参考文献：
  名称：

  1′,5′-Anhydro-l-ribo-hexitol Adenine Nucleic Acids (α-l-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World

  摘要：

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.

  DOI：

  10.1021/acs.joc.5b00406

文献信息

• Hybridization between “Six-Membered” Nucleic Acids:  RNA as a Universal Information System
  作者：Luc Kerremans、Guy Schepers、Jef Rozenski、Roger Busson、Arthur Van Aerschot、Piet Herdewijn

  DOI：10.1021/ol016183r

  日期：2001.12.1

  [GRAPHICS]Within the polyA:polyT recognition system, cross-pairing between several nucleic acids with a phosphorylated six-membered carbohydrate (mimic) as repeating unit in the backbone structure has been observed. All investigated nucleic acids (except for beta -homo-DNA) hybridize with RNA, leaving RNA as a versatile biopolymer for informational transfer.