怀俄苷 | 52662-10-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 怀俄苷
• 中文别名: 4,6-二甲基-3-(β-D-呋喃核糖基)-3,4-二氢-9H-咪唑并[1,2-a]嘌呤-9-酮
• 英文名称: wyosine
• 英文别名: 3-β-D-ribofuranosylwye；Wyosin；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6-dimethylimidazo[1,2-a]purin-9-one
• CAS: 52662-10-9
• 化学式: C₁₄H₁₇N₅O₅
• 分子量: 335.319
• InChiKey: JCZSFCLRSONYLH-QYVSTXNMSA-N

物化性质

• 沸点：
  827.6±75.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  怀俄苷 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 生成 3-methylguanosine
  参考文献：
  名称：

  A novel route to 3-methylguanosine by chemical degradation of wyosine

  摘要：

  DOI：

  10.1016/s0040-4039(00)80445-1
• 作为产物：
  描述：

  3,4-Dihydro-4,6-dimethyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-imidazo<1,2-a>purin-9-one 在 氨 作用下， 以88%的产率得到怀俄苷
  参考文献：
  名称：

  An efficient synthesis of y-nucleoside (wyosine) by regiospecific methylation of n4-desmethylwyosine using organozinc reagent

  摘要：

  DOI：

  10.1016/s0040-4039(00)95491-1

文献信息

• Structures of condensed tricyclic nucleosides of phenylalanine transfer ribonucleic acids
  作者：Taisuke Itaya、Tae Kanai

  DOI：10.1016/s0040-4039(99)01624-x

  日期：1999.11

  The unstable minor nucleosides, wyosine, wybutosine, and β-hydroxywybutosine, were isolated from tRNAs in sufficient amounts for determination of their structures.

  从tRNA中分离出足以确定其结构的不稳定次要核苷，wyosine，wybutosine和β-hydroxywybutosine。
• Structure of Wyosine, the Condensed Tricyclic Nucleoside of Torula Yeast Phenylalanine Transfer Ribonucleic Acid.
  作者：Taisuke Itaya、Tae Kanai、Takehiko Sawada

  DOI：10.1248/cpb.50.547

  日期：——

  nuclease P1/alkaline phosphatase. The nucleoside mixture thus obtained was purified by reversed-phase HPLC, providing wyosine (70 microg). Comparison of this nucleoside with a chemically synthesized authentic sample has unambiguously established that the structure of wyosine is 4,6-dimethyl-3-beta-D-ribofuranosyl-3,4-dihydro-9H-imidazo[1,2-a]purin-9-one (2).

  酶消化和反相色谱相结合，大规模分离了曲霉酵母tRNA（Phe）的次要核苷酪氨酸：含酪氨酸的核苷酸部分，通过部分消化未分离的tRNA（1 g）获得用核酸酶P1将其用反相柱色谱法浓缩，然后用核酸酶P1 /碱性磷酸酶完全消化。如此获得的核苷混合物通过反相HPLC纯化，提供了酪氨酸（70微克）。将该核苷与化学合成的真实样品进行比较已明确确定，该肌苷的结构为4,6-二甲基-3-β-D-呋喃核糖基-3,4-二氢-9H-咪唑并[1,2-a]嘌呤-9一（2）。
• Synthesis of 7-methyl-3-.BETA.-D-ribofuranosylwye, the most probable structure for the fluorescent nucleoside isolated from archaebacterial transfer ribonucleic acids.
  作者：Taisuke Itaya

  DOI：10.1248/cpb.35.4372

  日期：——

  3-β-D-Ribofuranosylwye (2a) was converted into 7-methyl-3-β-D-ribofuranosylwye (2b) through the 2', 3', 5'-tri-O-acetate by formylation with POCl3 and HCONMe2 followed by catalytic hydrogenolysis.

  3-β-D-Ribofuranosylwye (2a) 通过 2'，3'，5'-三-O-乙酸酯经 POCl3 和 HCONMe2 甲酰化转化为 7-甲基-3-β-D-呋喃核糖基 wye (2b)，然后催化氢解。
• A simple synthesis of 3-β-<scp>D</scp>-ribofuranosylwye and the stability of its glycosidic bond
  作者：Taisuke Itaya、Tomoko Watanabe、Hiroo Matsumoto

  DOI：10.1039/c39800001158

  日期：——

  Treatment of 5-(methylamino)-1-β-D-ribofuranosylimidazole-4-carboxamide (3) with CNBr followed by cyclization and reaction with bromoacetone gave 3-β-D-ribofuranosylwye (2) whose glycosidic bond was cleaved rapidly in acidic or alkaline solution, but was fairly stable at pH 5–8·5 at 37 °C.

  用CNBr处理5-（甲基氨基）-1 - β - D-呋喃核糖嘧啶-4-羧酰胺（3），然后环化并与溴丙酮反应，得到3- β - D-呋喃呋喃糖基wye（2），其糖苷键在酸性条件下迅速断裂或碱性溶液，但在37°C的pH 5–8·5下相当稳定。
• Synthesis of 7-methyl-3-.BETA.-D-ribofuranosylwye, the putative structure for the hypermodified nucleoside isolated from archaebacterial transfar ribonucleic acids.
  作者：Taisuke ITAYA、Masatoshi MORISUE、Motoko TAKEDA、Yukinari KUMAZAWA

  DOI：10.1248/cpb.38.2656

  日期：——

  The Vilsmeier-Haack reaction of 3-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl)wye (7c) followed successively by reduction with sodium borohydride and catalytic hydrogenolysis afforded the 7-methyl derivative 12c, which provided the title compound 12a on deprotection. Compound 12c was more effectively produced by direct hydrogenolysis of the 7-formyl derivative 8c, especially by use of Pearlman's catalyst. Similar treatment of 1-benzyl-7-formylwye (14) led to a better synthesis of 7-methylwye (1b), the fluorescent base isolated from Archabacterial transfer ribonucleic acids. Although hydrogenolysis of the 6-formyl compound 11 took place smoothly even over ordinary palladium on charcoal to afford 12c, this route had a bottleneck in the step of transformation of 8c into 11.Compound 12a proved to be highly sensitive to acidic hydrolysis at the glycosyl bond and the rate determined in 0.1N hydrochloric acid at 25°Cwas virtually the same as that of 3-β-D-ribofuranosylwye (7a).

  通过 3-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)黑麦（7c）的 Vilsmeier-Haack 反应，然后依次用硼氢化钠还原和催化氢解，得到了 7-甲基衍生物 12c，该衍生物经脱保护后得到了标题化合物 12a。通过直接氢解 7-甲酰基衍生物 8c，特别是使用珀尔曼催化剂，可以更有效地生成化合物 12c。对 1-苄基-7-甲酰基黑麦草碱（14）进行类似处理后，可以更好地合成 7-甲基黑麦草碱（1b），这种荧光碱是从古细菌转移核糖核酸中分离出来的。化合物 12a 被证明对糖基键的酸性水解非常敏感，在 25°C 的 0.1N 盐酸中测定的速率与 3-β-D-ribofuranosylwye (7a) 几乎相同。