[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]2-氨基乙酸酯 | 35985-26-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 中文名称: [[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]2-氨基乙酸酯
• 英文名称: glycyl adenylate
• 英文别名: Gly-O-AMP；[5']adenylic acid glycine anhydride；[5']Adenylsaeure-glycin-anhydrid；Glycyl-adenosine-5'-phosphate；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2-azaniumylacetyl) phosphate
• CAS: 35985-26-3
• 化学式: C₁₂H₁₇N₆O₈P
• 分子量: 404.276
• InChiKey: HROXHMRQKGGIFT-JJNLEZRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  218
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  水 、 [[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]2-氨基乙酸酯 生成 5'-腺嘌呤核苷酸 、 聚甘氨酸
  参考文献：
  名称：

  Moldave et al., Journal of Biological Chemistry, 1959, vol. 234, p. 841,843

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-腺嘌呤核苷酸 在 吡啶 、 钯 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 生成 [[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲氧基-羟基磷酰]2-氨基乙酸酯
  参考文献：
  名称：

  Moldave et al., Journal of Biological Chemistry, 1959, vol. 234, p. 841,843

  摘要：

  DOI：

文献信息

• Amino Acid Dependent Formation of Phosphate Anhydrides in Water Mediated by Carbonyl Sulfide
  作者：Luke J. Leman、Leslie E. Orgel、M. Reza Ghadiri

  DOI：10.1021/ja056036e

  日期：2006.1.1

  an efficient condensing agent in the context of phosphate chemistry in aqueous solutions. We report that high-energy aminoacyl-phosphate anhydrides and aminoacyl adenylates are generated in solutions containing amino acids, COS, and the corresponding phosphate molecule. We further show that the mixed anhydrides of amino acids and inorganic phosphate are phosphorylating agents, producing pyrophosphate

  硫化羰 (COS) 是火山气体排放和星际气体云的组成部分，在水溶液中的磷酸盐化学背景下被证明是一种有效的冷凝剂。我们报告说，在含有氨基酸、COS 和相应的磷酸盐分子的溶液中会产生高能氨酰磷酸酐和氨酰腺苷酸。我们进一步表明，氨基酸和无机磷酸盐的混合酸酐是磷酸化剂，在 Ca2+ 沉淀存在的情况下，焦磷酸盐的产率高于 30%。这里报道的磷酸的氨基酸依赖性激活与肽的产生同时发生，表明这两个反应可能在益生元地球上共享一个共同的中间体。
• Characterization of the Saframycin A Gene Cluster from<i>Streptomyces lavendulae</i>NRRL 11002 Revealing a Nonribosomal Peptide Synthetase System for Assembling the Unusual Tetrapeptidyl Skeleton in an Iterative Manner
  作者：Lei Li、Wei Deng、Jie Song、Wei Ding、Qun-Fei Zhao、Chao Peng、Wei-Wen Song、Gong-Li Tang、Wen Liu

  DOI：10.1128/jb.00826-07

  日期：2008.1

  tetrahydroisoquinoline family of antibiotics, and its core is structurally similar to the core of ecteinascidin 743, which is a highly potent antitumor drug isolated from a marine tunicate. In this study, the biosynthetic gene cluster for SFM-A was cloned and localized to a 62-kb contiguous DNA region. Sequence analysis revealed 30 genes that constitute the SFM-A gene cluster, encoding an unusual nonribosomal

  SAframycin A (SFM-A) 由 Streptomyces lavendulae NRRL 11002 生产，属于四氢异喹啉类抗生素，其核心结构类似于海鞘素 743 的核心，后者是一种从海洋被囊类动物中分离的高效抗肿瘤药物。在这项研究中，SFM-A 的生物合成基因簇被克隆并定位到 62-kb 的连续 DNA 区域。序列分析揭示了构成 SFM-A 基因簇的 30 个基因，这些基因编码一种不寻常的非核糖体肽合成酶 (NRPS) 系统以及定制酶以及调节和抗性蛋白。该 NRPS 系统腺苷酸化特异性的底物预测和体外表征结果支持最后一个模块以迭代方式作用以形成四肽基中间体并且不适用共线性规则的假设。尽管这种机制不同于为 SFM-A 类似物 SFM-Mx1 和 SAfracin B (SAC-B) 提出的机制，但基于这些系统的高度相似性，它们很可能具有我们在此处描述的共同生物合成机制。在 SAC-B
• Moriguchi, Tomohisa; Yanagi, Terukazu; Wada, Takeshi, Journal of the Chemical Society. Perkin transactions I, 1999, # 13, p. 1859 - 1865
  作者：Moriguchi, Tomohisa、Yanagi, Terukazu、Wada, Takeshi、Sekine, Mitsuo

  DOI：——

  日期：——
• McCorquodale; Mueller, Archives of Biochemistry, 1958, vol. 77, p. 13,14
  作者：McCorquodale、Mueller

  DOI：——

  日期：——
• The dhb Operon of Bacillus subtilisEncodes the Biosynthetic Template for the Catecholic Siderophore 2,3-Dihydroxybenzoate-Glycine-Threonine Trimeric Ester Bacillibactin
  作者：Jürgen J. May、Thomas M. Wendrich、Mohamed A. Marahiel

  DOI：10.1074/jbc.m009140200

  日期：2001.3

  Bacillus subtilis was reported to produce the catecholic siderophore itoic acid (2,3-dihydroxybenzoate (DHB)-glycine) in response to iron deprivation, However, by inspecting the DNA sequences of the genes dhbE, dhbB, and dhbF as annotated by the B, subtilis genome project to encode the synthetase complex for the siderophore assembly, various sequence errors within the dhbF gene were predicted and confirmed by re-sequencing. According to the corrected sequence, dhbF encodes a dimodular instead of a monomodular nonribosomal peptide synthetase, We have heterologously expressed, purified, and assayed the substrate selectivity of the recombinant proteins DhbB, DhbE, and DhbF, DhbE, a stand-alone adenylation domain of 59.9 kDa, activates, in an ATP-dependent reaction, I)HB, which is subsequently transferred to the free thiol group of the cofactor phosphopantetheine of the bifunctional isochorismate lyase/aryl carrier protein DhbB, The third synthetase, DhbF, is a dimodular nonribosomal peptide synthetase of 264 kDa that specifically adenylates threonine and, to a lesser extent, glycine and that covalently loads both amino acids onto their corresponding peptidyl carrier domains. To functionally link the dhb gene cluster to siderophore synthesis, we have disrupted the dhbF gene. Comparative mass spectrometric analysis of culture extracts from both the wild type and the dhbF mutant led to the identification of a mass peak at mit 881 ([M-H](1-)) that corresponds to a cyclic trimeric ester of DHB-glycine-threonine.