1,5-anhydro-2-(adenin-9-yl)-2,3-dideoxy-D-glucitol | 383859-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,5-anhydro-2-(adenin-9-yl)-2,3-dideoxy-D-glucitol
• 英文别名: (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydropyran-3-ol；(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxan-3-ol
• CAS: 383859-45-8
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: FVSBOJWVDIPQPA-GJMOJQLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-(adenin-9-yl)-2,3-dideoxy-D-glucitol 在 吡啶 、 三甲基氯硅烷 作用下， 反应 60.0h， 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：

  Hybridization between “Six-Membered” Nucleic Acids:  RNA as a Universal Information System

  摘要：

  [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.

  DOI：

  10.1021/ol016183r
• 作为产物：
  描述：

  腺嘌呤 在 palladium dihydroxide 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 环己烯 为溶剂， 反应 44.0h， 生成 1,5-anhydro-2-(adenin-9-yl)-2,3-dideoxy-D-glucitol
  参考文献：
  名称：

  Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-d-ribohexitol Nucleosides)

  摘要：

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.

  DOI：

  10.1021/jo961982m

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.
• Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-<scp>d</scp>-ribohexitol Nucleosides)
  作者：Nafizal Hossain、Jef Rozenski、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jo961982m

  日期：1997.4.1

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.
• 1′,5′-Anhydro-<scp>l</scp>-<i>ribo</i>-hexitol Adenine Nucleic Acids (α-<scp>l</scp>-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World
  作者：Daniele D’Alonzo、Mathy Froeyen、Guy Schepers、Giovanni Di Fabio、Arthur Van Aerschot、Piet Herdewijn、Giovanni Palumbo、Annalisa Guaragna

  DOI：10.1021/acs.joc.5b00406

  日期：2015.5.15

  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.