1,2-O-isopropylidene-α-D-<3-2H>ribofuranose | 99232-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-α-D-<3-2H>ribofuranose
• 英文别名: 1,2-O-isopropylidene-α-D-ribofuranose-3-d
• CAS: 99232-91-4
• 化学式: C₈H₁₄O₅
• 分子量: 191.188
• InChiKey: JAUQZVBVVJJRKM-MWVFSBTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.78
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-D-<3-2H>ribofuranose 在 吡啶 、 氯化亚砜 、 硫酸 、 氨 、 四氯化锡 作用下， 以 甲醇 、 六甲基磷酰三胺 、 溶剂黄146 、 乙腈 为溶剂， 反应 20.0h， 生成 5'-chloro-5'-deoxyadenosine-3'-d
  参考文献：
  名称：

  Mechanism of action of S-adenosyl-L-homocysteine hydrolase. Measurement of kinetic isotope effects using adenosine-3'-d and S-adenosyl-L-homocysteine-3'-d as substrates

  摘要：

  DOI：

  10.1021/ja00311a066
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-β-D-(3-2H)-mannose 在 sodium tetrahydroborate 、 sodium periodate 、 Dowex 50W-X₄-200 resin 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 1,2-O-isopropylidene-α-D-<3-2H>ribofuranose
  参考文献：
  名称：

  Mechanism of action of S-adenosyl-L-homocysteine hydrolase. Measurement of kinetic isotope effects using adenosine-3'-d and S-adenosyl-L-homocysteine-3'-d as substrates

  摘要：

  DOI：

  10.1021/ja00311a066

文献信息

• Studies on the Stereoselective Synthesis of Deuterated D-Ribose Derivatives
  作者：Mrinal K. Kundu、Andras Földesi、Jyoti Chattopadhyaya

  DOI：10.1002/hlca.200390062

  日期：2003.3

  as the key reaction. For C(5), two different routes were envisaged: on the one hand, deuterated achiral reagent was treated with a conformationally locked sugar moiety 15, while, on the other, chiral protonated sources were used to transfer the H-atom to a C(5)-deuterated aldehyde 18. In all cases, enantiomeric and isotopic purities were found to be as high as >97% as determined by NMR spectroscopy.

  鉴于H原子在戊糖残基上以立体选择性/立体特异性方式通过其稳定同位素2 H进行位点特异性取代的重要性，从而减少了1D和2D同核和异核相关区域中的光谱过度拥挤寡核苷酸DNA和-RNA的光谱，总是需要开发在核糖的不同位点掺入2 H的新方法。C（2）-和（5 R）-和（5 S）-3，5-氘代核糖衍生物已被设想用于将多标记核苷位点特异性掺入寡聚体中，以利于通过NMR光谱阐明其结构。适当的衍生化后，所有合成均从D-葡萄糖开始。在C（2）的情况下，掺入> 97原子％的同位素，采用C（2）处的构型反转作为关键反应。对于C（5），设想了两种不同的途径：一方面，使用构象锁定的糖部分15处理氘代非手性试剂，另一方面，使用手性质子化来源将H原子转移至C （5）氘化的醛18。在所有情况下，通过NMR光谱测定，发现对映体和同位素纯度高达> 97％。
• Escherichia coli imidazoleglycerol phosphate dehydratase: spectroscopic characterization of the enzymic product and the steric course of the reaction
  作者：Aulma R. Parker、Jeffrey A. Moore、John M. Schwab、V. Jo Davisson

  DOI：10.1021/ja00148a001

  日期：1995.11

  Recombinant strains of Escherichia coli have been developed for the high-level production of imidazoleglycerol phosphate dehydratase (IGPD) and imidazoleacetol phosphate aminotransferase (IAP aminotransferase). These protein sources facilitated the determination of the IGPD reaction stereochemistry and enabled the development of a continuous spectrophotometric enzyme assay for the IGPD reaction. D-erythro-IGP and D-erythro-[3-H-2]IGP were generated using a chemoenzymatic approach. D-((-))-[3-H-2]Ribose5-phosphate was prepared synthetically, starting from diacetone-D-glucose, and converted enzymatically to D-erythro-[3-H-2]IGP. In separate reactions, D-erythro-IGP and D-erythro-[3-H-2]IGP were converted to IAP using E. coli IGPD, The resulting IAP was transformed directly to histidinol using the coupled activities of E, coli IAP aminotransferase and histidinol phosphate phosphatase. The enzymatically generated histidinol samples were analyzed by H-1 and 2H NMR and compared to a synthetically prepared sample of (2S*,3S*)-[3-H-2]histidinol. This analysis demonstrated that the E. coli IGPD reaction proceeds with inversion of configuration at C-3, and the proton added to C-3 of IAP during the course of the dehydration is derived from the solvent. The observed stereochemical outcome is consistent with the idea that if the IGPD reaction proceeds through an enol intermediate, then tautomerization of the enol to IAP must be enzyme-mediated, The product of the IGPD reaction, IAP, has been characterized by NMR spectroscopy in aqueous solution. IAP undergoes rapid exchange of the C-3 protons with the bulk medium and exists as a mixture of the ketone and its hydrate (a geminal diol). Additional solution chemistry of IAP was observed using UV-vis and EPR spectroscopy and is consistent with the idea that IAP coordinates to Mn2+ in a bi- or tridentate fashion in aqueous solutions.
• Baker, Stephen J.; Young, Douglas W., Journal of labelled compounds and radiopharmaceuticals, 2000, vol. 43, # 10, p. 1022 - 1032
  作者：Baker, Stephen J.、Young, Douglas W.

  DOI：——

  日期：——