N,N-dimethylguanosine 5'-phosphate | 4214-21-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: N,N-dimethylguanosine 5'-phosphate
• 英文别名: N²,N²-dimethyl-[5']guanylic acid；N²-Dimethylguanosin-5'-phosphorsaeure；2-N,N-Dimethylguanosin-5'-phosphat；N(2),N(2)-dimethylguanosine 5'-monophosphate；[(2R,3S,4R,5R)-5-[2-(dimethylamino)-6-oxo-1H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 4214-21-5
• 化学式: C₁₂H₁₈N₅O₈P
• 分子量: 391.277
• InChiKey: IWJFVRMOIKWYNZ-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  179
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N-dimethylguanosine 5'-phosphate 在 三辛胺 、 2,2'-二硫二吡啶 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 5'-O-(imidolylphospho)-2-N,2-N,7-trimethylguanosine
  参考文献：
  名称：

  Chemical Synthesis of a 5‘-Terminal TMG-Capped Triribonucleotide m₃^2,2,7G^5‘pppAmpUmpA of U1 RNA

  摘要：

  The 5'-terminal TMG-capped triribonucleotide, m(3)(2,2,7)G(5')pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2'-O-methylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4-monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm(3)(2,2,7)G. The target TMG-capped tetramer, m(3)(2,2,7)G(5')pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5'-terminal diphosphate species, pp(AMMTr)mpUmpA, with Im-pm(3)(2,2,7)G followed by treatment with 80% acetic acid. The structure of m(3)(2,2,7)G(5')pppAmpUmpA was characterized by H-1 and P-31 NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.

  DOI：

  10.1021/jo952263v
• 作为产物：
  描述：

  2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷 在 sodium hydroxide 、 水 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 4.33h， 生成 N,N-dimethylguanosine 5'-phosphate
  参考文献：
  名称：

  Chemical Synthesis of a 5‘-Terminal TMG-Capped Triribonucleotide m₃^2,2,7G^5‘pppAmpUmpA of U1 RNA

  摘要：

  The 5'-terminal TMG-capped triribonucleotide, m(3)(2,2,7)G(5')pppAmpUmpA, has been synthesized by condensation of an appropriately protected triribonucleotide derivative of ppAmpUmpA with a new TMG-capping reagent. During this total synthesis, it was found that the regioselective 2'-O-methylation of 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-N-(4-monomethoxytrityl)adenosine was achieved by use of MeI/Ag2O without affecting the base moiety. A new route to 2-N,2-N-dimethylguanosine from guanosine via a three-step reaction has also been developed by reductive methylation using paraformaldehyde and sodium cyanoborohydride. These key intermediates were used as starting materials for the construction of a fully protected derivative of pAmpUmpA and a TMG-capping reagent of Im-pm(3)(2,2,7)G. The target TMG-capped tetramer, m(3)(2,2,7)G(5')pppAmpUmpA, was synthesized by condensation of a partially protected triribonucleotide 5'-terminal diphosphate species, pp(AMMTr)mpUmpA, with Im-pm(3)(2,2,7)G followed by treatment with 80% acetic acid. The structure of m(3)(2,2,7)G(5')pppAmpUmpA was characterized by H-1 and P-31 NMR spectroscopy as well as enzymatic assay using snake venom phosphodiesterase, calf intestinal phosphatase, and nuclease P1.

  DOI：

  10.1021/jo952263v

文献信息

• DARZYNKIEWICZ, EDWARD;STEPINSKI, JANUSZ;TAHARA, STANLEY M.;STOLARSKI, RYS+, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 599-618
  作者：DARZYNKIEWICZ, EDWARD、STEPINSKI, JANUSZ、TAHARA, STANLEY M.、STOLARSKI, RYS+

  DOI：——

  日期：——
• Solid-phase synthesis of a 5′-terminal TMG-capped trinucleotide block of U1 snRNA
  作者：Michinori Kadokura、Takeshi Wada、Kohji Seio、Tomohisa Moriguchi、Jochen Huber、Reinhard Lührmann、Mitsuo Sekine

  DOI：10.1016/s0040-4039(01)01941-4

  日期：2001.12

  A 5'-terminal 2,2,7-trimethylguanosine-capped trinucleotide block (m(3)(2,2,7)G(5')pppAmpUmpA) was successfully synthesized on a highly cross-linked polystyrene resin by a new method for introduction of the first nucleoside onto the resin and a newly developed pyrophosphorylating agent having a benzotriazolyloxy substitutent as the leaving group. (C) 2001 Published by Elsevier Science Ltd.
• De novo DNA cytosine methyltransferase genes, polypeptides and uses thereof
  申请人：The General Hospital Corporation

  公开号：US20040234997A1

  公开（公告）日：2004-11-25

  De novo DNA cytosine methyltransferase polynucleotides and polypeptides and methods for producing said polypeptides are disclosed. Also disclosed are methods for utilizing de novo DNA cytosine methyltransferase polynucleotides and polypeptides in diagnostic assays, in vitro DNA methylation assays for screening agonists and antagonists, and therapeutic applications such as the treatment of neoplastic disorders.
• NOVEL HUMAN ANDROGEN RECEPTOR ALTERNATIVE SPLICE VARIANTS AS BIOMARKERS AND THERAPEUTIC TARGETS
  申请人：Qiu Yun

  公开号：US20100068802A1

  公开（公告）日：2010-03-18

  The present invention relates to novel androgen receptor splice variants (AR3, AR4, AR4b, AR5 and AR8) and variants and fragments thereof which have a role in the progression of androgen independent prostate cancer. The invention further relates to compositions and methods which can be used to identify and treat prostate cancer based on these novel androgen receptor splice variants, as well as methods for screening agents which modulate the activity and/or expression of the androgen receptor splice variants. Vectors, host cells and recombinant methods for producing the same and transgenic animals are also provided.
• HUMAN ANDROGEN RECEPTOR ALTERNATIVE SPLICE VARIANTS
  申请人：Qiu Yun

  公开号：US20120156770A1

  公开（公告）日：2012-06-21

  The present invention relates to novel androgen receptor splice variants (AR3, AR4, AR4b, AR5 and AR8) and variants and fragments thereof which have a role in the progression of androgen independent prostate cancer. The invention further relates to compositions and methods which can be used to identify and treat prostate cancer based on these novel androgen receptor splice variants, as well as methods for screening agents which modulate the activity and/or expression of the androgen receptor splice variants. Vectors, host cells and recombinant methods for producing the same and transgenic animals are also provided.