2-Amino-6-mercapto-9-(β-D-xylofuranosyl)purine | 26017-62-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-Amino-6-mercapto-9-(β-D-xylofuranosyl)purine
• 英文别名: Thioguanosin；2-amino-9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
• CAS: 26017-62-9
• 化学式: C₁₀H₁₃N₅O₄S
• 分子量: 299.31
• InChiKey: OTDJAMXESTUWLO-FTWQFJAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 三甲基氯硅烷 、 sodium methylate 、 四氯化锡 、 硫脲 、 六甲基二硅氮烷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.33h， 生成 2-Amino-6-mercapto-9-(β-D-xylofuranosyl)purine
  参考文献：
  名称：

  核酸和相关类似物中五个天然碱基的α-和β-D-木呋喃糖基核苷的系统合成和生物学评估。

  摘要：

  天然存在的核苷的α-和β-D-木呋喃糖基类似物，以及其他D-木呋喃糖基衍生物，已成为其生物学（即抗病毒抗代谢和抑制细胞生长）特性的系统合成和研究对象。通过将嘌呤和嘧啶糖苷配基与过酰化的1-O-乙酰基-α-D-木呋喃糖基糖基化，然后除去保护基团来制备β端基异构体。通过使用2-氨基或2-巯基-α-D-木呋喃[1'，2'：4,5] -2-恶唑啉为起始原料的多步合成法获得α-端基异构体。测试了木呋喃糖基核苷对多种RNA和DNA病毒的活性以及对细胞生长和大分子合成的抑制作用。9-（β-D-木呋喃糖基）腺嘌呤三种化合物

  DOI：

  10.1021/jm00152a007

文献信息

• Oligonucleotides having chiral phosphorus linkages
  申请人：——

  公开号：US20010008936A1

  公开（公告）日：2001-07-19

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN 2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3′ position of a xylonucleotide. The reaction proceeds via inversion at the 3′ position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  本发明提供了具有高度纯的手性Sp磷酸硫酯、手性Rp磷酸硫酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯键的序列特异性寡核苷酸。新型寡核苷酸通过对木糖核苷酸的3'位置进行立体特异性的SN2亲核攻击制备而成，反应通过在木糖反应物种的3'位置进行反转，从而将磷酸二酯、磷酸硫酯、磷酸胺酯、磷酸三酯或烷基膦酸酯连接的核糖核苷糖基团并入寡核苷酸中。
• Monomers for preparation of oligonucleotides having chiral phosphorus
  申请人：ISIS Pharmaceuticals

  公开号：US05212295A1

  公开（公告）日：1993-05-18

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN.sub.2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3' position of a xylonucleotide. The reaction proceeds via inversion at the 3' position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  提供具有高度纯度的手性Sp硫代酸酯、手性Rp硫代酸酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯连接的序列特异性寡核苷酸。通过对木糖核苷酸的3'位点进行立体特异性的SN.sub.2亲核攻击，制备了这种新型寡核苷酸。反应通过在木糖反应物种的3'位点发生反转，将磷酸二酯、硫代酸酯、磷酰胺酸酯、磷酸三酯或烷基膦酸酯连接的核糖糖基结构并入寡核苷酸中。
• Process for preparing oligonucleotides having chiral phosphorus linkages
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US05521302A1

  公开（公告）日：1996-05-28

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN.sub.2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3' position of a xylonucleotide. The reaction proceeds via inversion at the 3' position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  提供具有高度纯度的手性Sp磷酸硫酯、手性Rp磷酸硫酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯链的序列特异性寡核苷酸。这些新型寡核苷酸是通过对木糖核苷酸的3'位点进行立体特异性的SN.sub.2亲核攻击来制备的，反应通过在木糖反应物种的3'位点发生反转，将磷酸二酯、磷酸硫酯、磷酰胺酸酯、磷酸三酯或烷基膦酸酯连接的核糖核苷糖基团并入寡核苷酸中。
• Nucleotides having chiral phosphorus linkages
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06500945B2

  公开（公告）日：2002-12-31

  Sequence-specific oligonucleotides are provided having substantially pure chiral Sp phosphorothioate, chiral Rp phosphorothioate, chiral Sp alkylphosphonate, chiral Rp alkylphosphonate, chiral Sp phosphoamidate, chiral Rp phosphoamidate, chiral Sp phosphotriester, and chiral Rp phosphotriester linkages. The novel oligonucleotides are prepared via a stereospecific SN2 nucleophilic attack of a phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate anion on the 3′ position of a xylonucleotide. The reaction proceeds via inversion at the 3′ position of the xylo reactant species, resulting in the incorporation of phosphodiester, phosphorothioate, phosphoramidate, phosphotriester or alkylphosphonate linked ribofuranosyl sugar moieties into the oligonucleotide.

  提供了具有高度纯度的手性Sp硫代酸酯、手性Rp硫代酸酯、手性Sp烷基膦酸酯、手性Rp烷基膦酸酯、手性Sp磷酰胺酸酯、手性Rp磷酰胺酸酯、手性Sp磷酸三酯和手性Rp磷酸三酯键的序列特异性寡核苷酸。通过对木糖核苷酸的3'位点进行立体特异性的SN2亲核攻击，制备了这种新型寡核苷酸。反应通过对木糖反应物种的3'位点的倒位进行，将磷酸二酯、硫代酸酯、磷酰胺酸酯、磷酸三酯或烷基膦酸酯连接的核糖苷糖基团并入寡核苷酸中。
• JANKOWSKI, ALEKSANDER J.;WISE, DEAN S. (JR);TOWNSEND, LEROY B., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 339-348
  作者：JANKOWSKI, ALEKSANDER J.、WISE, DEAN S. (JR)、TOWNSEND, LEROY B.

  DOI：——

  日期：——