lysyl adenylate | 35985-27-4

• 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
• 英文名称: lysyl adenylate
• 英文别名: Adenosine-5'-[lysyl-phosphate]；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] (2S)-2,6-diaminohexanoate
• CAS: 35985-27-4
• 化学式: C₁₆H₂₆N₇O₈P
• 分子量: 475.398
• InChiKey: RZWIOOBQBMRZTQ-OPYVMVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  244
• 氢给体数：
  6
• 氢受体数：
  14

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5’-三磷酸腺苷	ATP	56-65-5	C10H16N5O13P3	507.184

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Diadenosine triphosphate	5959-90-0	C20H27N10O16P3	756.413
  [[[[(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]氧基-羟基磷酰]氧基-羟基磷酰][(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基磷酸氢酯	Diadenosine tetraphosphate	5542-28-9	C20H28N10O19P4	836.393
  [(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[羟基-(羟基-膦酰氧基磷酰)氧基磷酰]氢磷酸酯	adenosine 5'-tetraphosphate	1062-98-2	C10H17N5O16P4	587.164
  ——	adenosine(2'-deoxyadenosine) 5',5'''-P1,P4-tetraphosphate	——	C20H28N10O18P4	820.394
  ——	adenosine(adenine arabinofuranoside) 5',5'''-P1,P4-tetraphosphate	——	C20H28N10O19P4	836.393
  ——	Ap4I	——	C20H27N9O20P4	837.378
  ——	adenosine(cytidine) 5',5'''-P1,P4-tetraphosphate	——	C19H28N8O20P4	812.368
  ——	adenosine(xanthosine) 5',5'''-P1,P4-tetraphosphate	——	C20H27N9O21P4	853.377
  ——	adenosine(guanosine) 5',5'''-P1,P4-(β,γ-methylene)tetraphosphate	——	C21H30N10O19P4	850.42
  ——	adenosine(8-bromoadenosine) 5',5'''-P1,P4-tetraphosphate	——	C20H27BrN10O19P4	915.289

反应信息

• 作为反应物：
  描述：

  lysyl adenylate 在 Sodium tripolyphosphate 、 zinc(II) chloride 作用下， 以52%的产率得到[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基]甲基[羟基-(羟基-膦酰氧基磷酰)氧基磷酰]氢磷酸酯
  参考文献：
  名称：

  Characterisation of stress protein LysU. Enzymic synthesis of diadenosine 5′,5‴-P¹,P⁴-tetraphosphate (Ap₄A) analogues by LysU

  摘要：

  The stress protein LysU (lysyl tRNA synthetase) has been purified from a recombinant strain of Escherichia coli expressing the plasmid pXLys5, and kinetically characterised. Preparative syntheses of analogues of the biologically important molecule diadenosine 5',5'''-P-1,P-4-tetraphosphate (Ap(4)A) are then achieved in good yield by enzyme catalysis, using purified LysU.

  DOI：

  10.1039/p19960002009
• 作为产物：
  描述：

  L-赖氨酸 、 5’-三磷酸腺苷 在 TRIS buffer pH 8 、 potassium chloride 、 magnesium chloride 、 zinc(II) chloride 作用下， 反应 2.5h， 生成 lysyl adenylate
  参考文献：
  名称：

  Characterisation of stress protein LysU. Enzymic synthesis of diadenosine 5′,5‴-P¹,P⁴-tetraphosphate (Ap₄A) analogues by LysU

  摘要：

  The stress protein LysU (lysyl tRNA synthetase) has been purified from a recombinant strain of Escherichia coli expressing the plasmid pXLys5, and kinetically characterised. Preparative syntheses of analogues of the biologically important molecule diadenosine 5',5'''-P-1,P-4-tetraphosphate (Ap(4)A) are then achieved in good yield by enzyme catalysis, using purified LysU.

  DOI：

  10.1039/p19960002009

文献信息

• Syntheses of stable, synthetic diadenosine polyphosphate analogues using recombinant histidine-tagged lysyl tRNA synthetase (LysU)
  作者：Michael Wright、M. Ameruddin Azhar、Ahmed Kamal、Andrew D. Miller

  DOI：10.1016/j.bmcl.2014.03.064

  日期：2014.5

  Recombinant Escherichia coli lysyl-tRNA synthase (LysU) has been previously utilised in the production of stabile, synthetic diadenosine polyphosphate (ApnA) analogues. Here we report on the extended use of a new recombinant histidine residue-tagged LysU as a tool for highly controlled phosphateAphosphate bond formation between nucleotides, avoiding the need for complex protecting group chemistries. Resulting high yielding tandem LysU-based biosynthetic-synthetic/synthetic-biosynthetic strategies emerge for the preparation of varieties of ApnA analogues directly from inexpensive natural nucleotides and nucleosides. Analogues so formed make a useful small library with which to probe ApnA activities in vitro and in vivo leading to the discovery of new, potentially potent biopharmaceuticals active against chronic pain and other chronic, high-burden disease states. (C) 2014 Published by Elsevier Ltd.
• Characterisation of stress protein LysU. Enzymic synthesis of diadenosine 5′,5‴-P¹,P⁴-tetraphosphate (Ap₄A) analogues by LysU
  作者：Maria-Elena Theoclitou、E. Pernilla L. Wittung、Alison D. Hindley、Talal S. H. El-Thaher、Andrew D. Miller

  DOI：10.1039/p19960002009

  日期：——

  The stress protein LysU (lysyl tRNA synthetase) has been purified from a recombinant strain of Escherichia coli expressing the plasmid pXLys5, and kinetically characterised. Preparative syntheses of analogues of the biologically important molecule diadenosine 5',5'''-P-1,P-4-tetraphosphate (Ap(4)A) are then achieved in good yield by enzyme catalysis, using purified LysU.