4-氨基-1-(2’,3’,5’-三-O-叔-丁基二甲基硅烷基-beta-D-呋喃核糖基)-咪唑并[4,5-a]吡啶 | 147212-86-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑[4，5-c]吡啶核糖核苷和核糖核苷酸
• 中文名称: 4-氨基-1-(2’,3’,5’-三-O-叔-丁基二甲基硅烷基-beta-D-呋喃核糖基)-咪唑并[4,5-a]吡啶
• 英文名称: 2',3',5'-O-tris(tert-butyldimethylsilyl)-3-deazaadenosine
• 英文别名: 4-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridine；4-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine；4-Amino-1-(2',3',5'-tri-O-tert-butyldimethylsilyl-b-D-ribofuranosyl)-imidazo[4,5-c]pyridine；1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]imidazo[4,5-c]pyridin-4-amine
• CAS: 147212-86-0
• 化学式: C₂₉H₅₆N₄O₄Si₃
• 分子量: 609.045
• InChiKey: SOGOMPJANKBXFD-IGGXFAESSA-N

物化性质

• 熔点：
  121-125°C
• 沸点：
  595.7±60.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-氨基-1-(2’,3’,5’-三-O-叔-丁基二甲基硅烷基-beta-D-呋喃核糖基)-咪唑并[4,5-a]吡啶 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以120 mg的产率得到3-脱氮腺苷
  参考文献：
  名称：

  核苷和核苷酸。116.通过5-乙炔基-1-β-D-呋喃呋喃基咪唑-4-羧酰胺或-腈的闭环，方便地合成3-脱氮杂腺苷，3-脱氮鸟苷和3-脱氮肌苷

  摘要：

  3-deazapurine核苷，3-deazainosine [1-β-D-呋喃呋喃基嘧啶并[4,5- c ] pyridin-4（5 H）-one（8）]，3-deazaguanosine [6-amino- 1-β-D-呋喃呋喃基咪唑并[4,5- c ]吡啶-4（5 H）-one（23）]和3-脱氮杂腺苷[4-氨基-1-β-D-呋喃呋喃基咪唑并[4,5- c]描述了[吡啶（29）]。该方法包括在咪唑环的4-位和5-位的取代基之间的闭环。5-乙炔基-1-β-D-呋喃呋喃基氨基咪唑-4-羧酰胺的处理（2），可以很容易地从AICA核糖苷中获得（1）），先后用二甲胺水溶液和乙酸水溶液，以64％的收率得到8。5-（2-羟基亚氨基乙基）-1-（2,3,5-三- ø -叔丁基二-β-d-D-呋喃核糖基）咪唑-4-甲酰胺（19）从合成3由治疗的二甲胺水溶液，接着由盐酸羟胺制成。通过苯基异氰酸酯实现19

  DOI：

  10.1016/s0040-4020(01)86259-1
• 作为产物：
  描述：

  2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine 在 吡啶 、 二(氰基苯)二氯化钯 、 二碘甲烷 、 potassium carbonate 、 乙二胺 、 三乙胺 、 对甲苯磺酰氯 、 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 63.25h， 生成 4-氨基-1-(2’,3’,5’-三-O-叔-丁基二甲基硅烷基-beta-D-呋喃核糖基)-咪唑并[4,5-a]吡啶
  参考文献：
  名称：

  Efficient Ribosomal Peptidyl Transfer Critically Relies on the Presence of the Ribose 2‘-OH at A2451 of 23S rRNA

  摘要：

  The ribosomal peptidyl transferase center is a ribozyme catalyzing peptide bond synthesis in all organisms. We applied a novel modified nucleoside interference approach to identify functional groups at 9 universally conserved active site residues. Owing to their immediate proximity to the chemical center, the 23S rRNA nucleosides A2451, U2506 and U2585 were of particular interest. Our study ruled out U2506 and U2585 as contributors of vital chemical groups for transpeptidation. In contrast the ribose 2'-OH of A2451 was identified as the prime ribosomal group with potential functional importance. This 2'-OH renders almost full catalytic power to the ribosome even when embedded into an active site of six neighboring 2'-deoxyribose nucleosides. These data highlight the unique functional role of the A2451 2'-OH for peptide bond synthesis among all other functional groups at the ribosomal peptidyl transferase active site.

  DOI：

  10.1021/ja0588454

文献信息

• Nucleosides and Nucleotides. 184. Synthesis and Conformational Investigation of Anti-Fixed 3-Deaza-3-halopurine Ribonucleosides¹^,²
  作者：Noriaki Minakawa、Naoshi Kojima、Akira Matsuda

  DOI：10.1021/jo990638x

  日期：1999.9.1

  A versatile synthetic route to 3-deaza-3-haloinosines 6-8 and 46, -adenosines 15-17 and 64, and -guanosines 25, 26, and 52 is described. 3-Deaza-3-chloro-, -bromo-, and -iodopurine ribonucleosides can be synthesized by treating the 3-deazapurine ribonucleosides with N-halosuccinimides. For the synthesis of 3-deaza-3-fluoropurine ribonucleosides, 5-formylimidazole-4-carboxamide ribosides 34 and 35 prepared from 5-iodoimidazole-4-carboxamide derivatives 29 and 31 were us ed as the key intermediates. The reaction of 34 and 35 with lithium (trimethylsilyl)acetylide and sodium cyanide, respectively, followed by appropriate manipulations gave 3-deaza-3-fluoroinosine derivative 46 and 3-deaza-3-fluoroguanosine derivative 52. 3-Deaza-3-fluoroadenosine (64) was also synthesized by selective reductive deamination of 4,6-diamino-7-fluoroimidazo[4,5-c]pyridine derivative 51, followed by deprotection. A conformational analysis using H-1 NMR and NOE experiments showed that the introduction of halogens (chloro, bromo, and iodo) into the 3-position of 3-deazapurine ribonucleosides forced fixation of the glycosyl torsion angle in the anti region, but did not-abnormally influence sugar puckering. On the other hand, 3-deaza-3-fluoropurine ribonucleosides should rotate freely around the glycosyl bond.
• Nucleosides and nucleotides. 114. A convenient method for the synthesis of 3-deazapurine nucleosides from AICA-Riboside
  作者：Noriaki Minakawa、Akira Matsuda

  DOI：10.1016/s0040-4039(00)61646-5

  日期：1993.1

  3-Deazapurine nucleosides, 3-deazainosine (6), 3-deazaguanosine (12), and 3-deazaadenosine (17), were synthesized from 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (2) or -4-carbonitrile (13), which were readily obtained from AICA-riboside, via intramolecular ring closure.
• Efficient Ribosomal Peptidyl Transfer Critically Relies on the Presence of the Ribose 2‘-OH at A2451 of 23S rRNA
  作者：Matthias D. Erlacher、Kathrin Lang、Brigitte Wotzel、Renate Rieder、Ronald Micura、Norbert Polacek

  DOI：10.1021/ja0588454

  日期：2006.4.5

  The ribosomal peptidyl transferase center is a ribozyme catalyzing peptide bond synthesis in all organisms. We applied a novel modified nucleoside interference approach to identify functional groups at 9 universally conserved active site residues. Owing to their immediate proximity to the chemical center, the 23S rRNA nucleosides A2451, U2506 and U2585 were of particular interest. Our study ruled out U2506 and U2585 as contributors of vital chemical groups for transpeptidation. In contrast the ribose 2'-OH of A2451 was identified as the prime ribosomal group with potential functional importance. This 2'-OH renders almost full catalytic power to the ribosome even when embedded into an active site of six neighboring 2'-deoxyribose nucleosides. These data highlight the unique functional role of the A2451 2'-OH for peptide bond synthesis among all other functional groups at the ribosomal peptidyl transferase active site.
• Nucleosides and nucleotides. 116. Convenient syntheses of 3-deazaadenosine, 3-deazaguanosine, and 3-deazainosine via ring closure of 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide or -carbonitrile
  作者：Noriaki Minakawa、Akira Matsuda

  DOI：10.1016/s0040-4020(01)86259-1

  日期：1993.1

  An easy chemical synthesis of 3-deazapurine nucleosides, 3-deazainosine [1-β-D-ribofuranosylimidazo[4,5-c]pyridin-4(5H)-one (8)], 3-deazaguanosine [6-amino-1-β-D-ribofuranosylimidazo[4,5-c]pyridin-4(5H)-one (23)], and 3-deazaadenosine [4-amino-1-β-D-ribofuranosylimidazo[4,5-c]pyridine (29)] is described. The approach consists of ring closure between substituents at 4- and 5-positions of the imidazole

  3-deazapurine核苷，3-deazainosine [1-β-D-呋喃呋喃基嘧啶并[4,5- c ] pyridin-4（5 H）-one（8）]，3-deazaguanosine [6-amino- 1-β-D-呋喃呋喃基咪唑并[4,5- c ]吡啶-4（5 H）-one（23）]和3-脱氮杂腺苷[4-氨基-1-β-D-呋喃呋喃基咪唑并[4,5- c]描述了[吡啶（29）]。该方法包括在咪唑环的4-位和5-位的取代基之间的闭环。5-乙炔基-1-β-D-呋喃呋喃基氨基咪唑-4-羧酰胺的处理（2），可以很容易地从AICA核糖苷中获得（1）），先后用二甲胺水溶液和乙酸水溶液，以64％的收率得到8。5-（2-羟基亚氨基乙基）-1-（2,3,5-三- ø -叔丁基二-β-d-D-呋喃核糖基）咪唑-4-甲酰胺（19）从合成3由治疗的二甲胺水溶液，接着由盐酸羟胺制成。通过苯基异氰酸酯实现19