phenylpropionyl-N-acetylcysteamine | 1443120-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylpropionyl-N-acetylcysteamine
• CAS: 1443120-38-4
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: RMXPSTZACDVABH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  phenylpropionyl-N-acetylcysteamine 、 teicoplanin A2-2 在 N-acyltransferase Orf₁₁ 作用下， 以 aq. buffer 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Multiple Complexes of Long Aliphatic N-Acyltransferases Lead to Synthesis of 2,6-Diacylated/2-Acyl-Substituted Glycopeptide Antibiotics, Effectively Killing Vancomycin-Resistant Enterococcus

  摘要：

  Teicoplanin A2-2 (Tei)/A40926 is the last-line antibiotic to treat multidrug-resistant Gram-positive bacterial infections, e.g., methicillinresistant Staphylococcus aurcus (MRSA) and vancomycin-resistant enterococcus (VRE). This class of antibiotics is powered by the N-acyltransferase (NAT) Orf11*/Dbv8 through N-acylation on glucosamine at the central residue of Tei/A40926 pseudoaglycone. The NAT enzyme possesses enormous value in untapped applications; its advanced development is hampered largely due to a lack of structural information. In this report, we present eight high-resolution X-ray crystallographic unary, binary, and ternary complexes in order to decipher the molecular basis for NAT's functionality. The enzyme undergoes a multistage conformational change upon binding of acyl-CoA, thus allowing the uploading of Tei pseudoaglycone to enable the acyl-transfer reaction to take place in the occlusion between the N- and C-halves of the protein. The acyl moiety of acyl-CoA can be bulky or lengthy, allowing a large extent of diversity in new derivatives that can be formed upon its transfer. Vancomycin/synthetic acyl-N-acetyl cysteamine was not expected to be able to serve as a surrogate for an acyl acceptor/donor, respectively. Most strikingly, NAT can catalyze formation of 2-N,6-O-diacylated or C6 -> C2 acyl-substituted Tei analogues through an unusual 1,4-migration mechanism under stoichiometric/solvational reaction control, wherein selected representatives showed excellent biological activities, effectively counteracting major types (VanABC) of VRE.

  DOI：

  10.1021/ja504125v
• 作为产物：
  描述：

  N-乙酰基半胱胺 、 3-苯基丙酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 phenylpropionyl-N-acetylcysteamine
  参考文献：
  名称：

  Biosynthesis of tetraoxygenated phenylphenalenones in Wachendorfia thyrsiflora

  摘要：

  The biosynthetic origin of 1,2,5,6-tetraoxygenated phenylphenalenones and the sequence according to which their oxygen functionalities are introduced during the biosynthesis in Wachendorfia thyrsiflora were studied using two approaches. (1) Oxygenated phenylpropanoids were probed as substrates of recombinant W thyrsiflora polyketide synthase I (WtPKS1), which is involved in the diarylheptanoid and phenylphenalenone biosynthetic pathways, (2) Root cultures of W thyrsiflora were incubated with C-13-labelled precursors in an O-18(2) atmosphere to observe incorporation of the two isotopes at defined biosynthetic steps. NMR- and HRESIMS-based analyses were used to unravel the isotopologue composition of the biosynthetic products, lachnanthoside aglycone and its allophanyl glucoside. Current results suggest that the oxygen atoms decorating the phenalenone tricycle are introduced at different biosynthetic stages in the sequence O-1 -> O-2 -> O-5. In addition, the incubation of W. thyrsiflora root cultures with C-13-labelled lachnanthocarpone established a direct biosynthetic precursor-product relationship with I,2,5,6-tetraoxygenated phenylphenalenones. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.02.020