L-Ala coenzyme A thioester | 229484-28-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: L-Ala coenzyme A thioester
• 英文别名: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (2S)-2-aminopropanethioate
• CAS: 229484-28-0
• 化学式: C₂₄H₄₁N₈O₁₇P₃S
• 分子量: 838.62
• InChiKey: OIKPXGRGSUBNRF-IBNUZSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.4
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  415
• 氢给体数：
  10
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  N-Boc-L-Ala coenzyme A thioester 在 水 、 三氟乙酸 作用下， 反应 1.0h， 生成 L-Ala coenzyme A thioester
  参考文献：
  名称：

  Unraveling Terminal C-Domain-Mediated Condensation in Fungal Biosynthesis of Imidazoindolone Metabolites

  摘要：

  The fungal peptidyl alkaloids of the tryptoquialanine and fumiquinazoline families are nonribosomally assembled by annulation of the indole side chain of fumiquinazoline F (FQF) with an alaninyl or aminoisobutyryl unit by monomodular NRPS enzymes containing adenylation, thiolation, and condensation (A-T-C) domains. The Af12060 and Af12050 enzyme pair from Aspergillus fumigatus thereby converts FQF to FQA, while the homologous TqaH and TqaB enzyme pair from Penicillium aethiopicum makes the 2'-epi diastereomer of FQA, differing only in the stereochemistry of one of the C-N bonds formed in the annulation with L-Ala. To evaluate the basis for this stereochemical control, we have mixed and matched the flavoprotein oxygenases Af12060 and TqaH with the A-T-C modular enzymes Af12050 and TqaB to show that the NRPS enzymes control the stereochemical outcome. The terminal 50 kDa condensation domains of Af12050 and TqaB are solely responsible for the stereochemical control as shown both by making chimeric (e.g., A-T-C* and A*-T*-C) forms of these rnonomodular NRPS enzymes and by expression, purification, and assay of the excised C-domains. The Af12050 and TqaB condensation domains are thus a paired set of diastereospecific annulation catalysts that act on the fumiquinazoline F scaffold.

  DOI：

  10.1021/bi2004922