[3-2H]-1,2-O-isopropylidene-α-D-allofuranose | 99232-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-2H]-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: 1,2-O-isopropylidene-α-D-ribohexofuranose-3-d
• CAS: 99232-90-3
• 化学式: C₉H₁₆O₆
• 分子量: 221.214
• InChiKey: BGGCXQKYCBBHAH-WYPRSEDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [3-2H]-1,2-O-isopropylidene-α-D-allofuranose 在 硼氘化钠 、 sodium hydride 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 3,5-O-dibenzyl-1,2-O-isopropylidene-α-D-ribofuranose-3,5(R/S)-2H2
  参考文献：
  名称：

  Synthesis of partially-deuterated 2′-deoxyribonucleoside blocks and their incorporation into an oligo-DNA for simplification of overcrowding and selective enhancement of resolution and sensitivity in the 1H-NMR spectra

  摘要：

  The chemical synthesis of appropriately protected partially-deuterated 2'((R) under bar/(S) under bar), 3',5'((R) under bar/(S) under bar)-H-2(3)-2'-deoxyribonucleoside blocks [similar to 43 atom % H-2 at C5'((R) under bar), similar to 57 atom % H-2 at C5'((S) under bar); similar to 15 atom % H-2 at C2'((R) under bar, similar to 85 atom % H-2 at C2'((S) under bar) and >99 atom % H-2 at C3'] is reported. The availability of these deuterium labelled blocks on large scale has enabled the chemical assemblage of the deuterio isotopomeric 12 mer [d((C) double under bar(1)(G) double under bar(2)(C) double under bar(3)(G) double under bar(4)(A) double under bar(5)(A) double under bar(6)(T) double under bar(7)(T) double under bar(8)(C) double under bar(9)(G) double under bar(10)(C) double under bar(11)(G) double under bar(12))](2) DNA duplex by standard solid-phase synthesis protocol in order to demonstrate the usefulness of the new "NMR-window III" approach (see the following paper). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00905-3
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-β-D-(3-2H)-mannose 在 Dowex 50W-X₄-200 resin 作用下， 以 水 为溶剂， 反应 0.33h， 以78%的产率得到[3-2H]-1,2-O-isopropylidene-α-D-allofuranose
  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

• Stereochemical course of the Escherichia coli imidazole glycerol phosphate dehydratase reaction
  作者：Jeffrey A. Moore、Aulma R. Parker、V. Jo Davisson、John M. Schwab

  DOI：10.1021/ja00061a046

  日期：1993.4
• 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：——
• T1 and T2 relaxations of the 13C nuclei of deuterium‐labeled nucleosides
  作者：T. V. Maltseva、A. Földesi、J. Chattopadhyaya

  DOI：10.1002/(sici)1097-458x(199804)36:4<227::aid-omr266>3.3.co;2-0

  日期：1998.4