[3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]氧基膦酸 | 14075-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]氧基膦酸
• 英文名称: ribose-1-phosphate
• 英文别名: D-ribose-1-phosphate；D-Ribose 1-phosphate；[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl] dihydrogen phosphate
• CAS: 14075-00-4
• 化学式: C₅H₁₁O₈P
• 分子量: 230.111
• InChiKey: YXJDFQJKERBOBM-SOOFDHNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

制备方法与用途

D-呋喃核糖-1-二氢磷酸，亦称1-磷酸核糖，是尿苷磷酸化酶合成5-氟尿嘧啶（FUra）所需的物质。

反应信息

• 作为反应物：
  描述：

  [3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]氧基膦酸 、 8-氮鸟嘌呤 在 calf spleen purine nucleoside phosphatase 作用下， 生成 5-氨基-3-[3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-2H-三唑并[4,5-e]嘧啶-7-酮
  参考文献：
  名称：

  SPECTROSCOPIC AND KINETIC STUDIES OF INTERACTIONS OF CALF SPLEEN PURINE NUCLEOSIDE PHOSPHORYLASE WITH 8-AZAGUANINE, AND ITS 9-(2-PHOSPHONYLMETHOXYETHYL) DERIVATIVE

  摘要：

  Spectroscopic and kinetic studies of interactions of calf spleen purine nucleoside phosphorylase with 8-azaguanine, an excellent fluorescent/fluorogenic substrate for the synthetic pathway of the reaction, and its 9-(2-phosphonylmethoxyethyl) derivative, a bisubstrate analogue inhibitor, were carried out. The goal was to clarify the catalytic mechanism of the enzymatic reaction by identification of ionic/tautomeric forms of these ligands in the complex with PNP.

  DOI：

  10.1081/ncn-200060004
• 作为产物：
  描述：

  肌苷 在 potassium phosphate 作用下， 反应 3.0h， 以27.1 mmol的产率得到[3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]氧基膦酸
  参考文献：
  名称：

  Shirae, Hideyuki; Yokozeki, Kenzo; Kubota, Koji, Agricultural and Biological Chemistry, 1988, vol. 52, # 1, p. 295 - 296

  摘要：

  DOI：

文献信息

• Characterization of pyrimidine nucleoside phosphorylase of <i>Mycoplasma hyorhinis</i>: implications for the clinical efficacy of nucleoside analogues
  作者：Johan Vande Voorde、Federico Gago、Kristof Vrancken、Sandra Liekens、Jan Balzarini

  DOI：10.1042/bj20112225

  日期：2012.7.1

  In the present paper we demonstrate that the cytostatic and antiviral activity of pyrimidine nucleoside analogues is markedly decreased by a Mycoplasma hyorhinis infection and show that the phosphorolytic activity of the mycoplasmas is responsible for this. Since mycoplasmas are (i) an important cause of secondary infections in immunocompromised (e.g. HIV infected) patients and (ii) known to preferentially colonize tumour tissue in cancer patients, catabolic mycoplasma enzymes may compromise efficient chemotherapy of virus infections and cancer. In the genome of M. hyorhinis, a TP (thymidine phosphorylase) gene has been annotated. This gene was cloned, expressed in Escherichia coli and kinetically characterized. Whereas the mycoplasma TP efficiently catalyses the phosphorolysis of thymidine (Km=473 μM) and deoxyuridine (Km=578 μM), it prefers uridine (Km=92 μM) as a substrate. Our kinetic data and sequence analysis revealed that the annotated M. hyorhinis TP belongs to the NP (nucleoside phosphorylase)-II class PyNPs (pyrimidine NPs), and is distinct from the NP-II class TP and NP-I class UPs (uridine phosphorylases). M. hyorhinis PyNP also markedly differs from TP and UP in its substrate specificity towards therapeutic nucleoside analogues and susceptibility to clinically relevant drugs. Several kinetic properties of mycoplasma PyNP were explained by in silico analyses.

  在本文中，我们证明了嘧啶核苷类似物的细胞抑制和抗病毒活性会因解脲支原体感染而明显降低，并表明支原体的磷酸溶解活性是造成这种情况的原因。由于支原体（i）是免疫力低下（如艾滋病毒感染者）患者继发感染的重要原因，（ii）已知会优先定植于癌症患者的肿瘤组织，因此分解支原体酶可能会影响病毒感染和癌症化疗的效率。在潮霉素支原体的基因组中，有一个 TP（胸腺嘧啶磷酸化酶）基因。该基因已被克隆，并在大肠杆菌中表达和进行动力学鉴定。支原体 TP 能有效催化胸苷（Km=473 μM）和脱氧尿苷（Km=578 μM）的磷酸化，但它更喜欢尿苷（Km=92 μM）作为底物。我们的动力学数据和序列分析表明，注释的潮霉素 TP 属于 NP（核苷磷酸化酶）-II 类 PyNPs（嘧啶 NPs），有别于 NP-II 类 TP 和 NP-I 类 UPs（尿苷磷酸化酶）。在对治疗用核苷类似物的底物特异性和对临床相关药物的敏感性方面，土拉菲霉菌的 PyNP 也与 TP 和 UP 有明显不同。支原体 PyNP 的一些动力学特性已通过硅学分析得到解释。
• Reversible and in situ formation of organic arsenates and vanadates as organic phosphate mimics in enzymatic reactions: mechanistic investigation of aldol reactions and synthetic applications
  作者：Dale G. Drueckhammer、J. Robert Durrwachter、Richard L. Pederson、Debbie C. Crans、Lacy Daniels、Chi Huey Wong

  DOI：10.1021/jo00262a021

  日期：1989.1
• Anderson, Jack D.; Cottam, Howard B.; Larson, Steven B., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 439 - 453
  作者：Anderson, Jack D.、Cottam, Howard B.、Larson, Steven B.、Dee Nord, L.、Revankar, Ganapathi R.、Robins, Roland K.

  DOI：——

  日期：——
• ANDERSON, JACK D.;COTTAM, HOWARD B.;LARSON, STEVEN B.;NORD, L. DEE;REVANK+, J. HETEROCYCL. CHEM., 27,(1990) N, C. 439-453
  作者：ANDERSON, JACK D.、COTTAM, HOWARD B.、LARSON, STEVEN B.、NORD, L. DEE、REVANK+

  DOI：——

  日期：——
• Shirae, Hideyuki; Yokozeki, Kenzo; Kubota, Koji, Agricultural and Biological Chemistry, 1988, vol. 52, # 1, p. 295 - 296
  作者：Shirae, Hideyuki、Yokozeki, Kenzo、Kubota, Koji

  DOI：——

  日期：——