| 1073233-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1073233-00-7
• 化学式: C₅H₁₂O
• 分子量: 91.1259
• InChiKey: QPRQEDXDYOZYLA-OJWMFZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  6.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  在 N-甲基吗啉氧化物 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 (S)-2-(methyl-d3)butanal
  参考文献：
  名称：

  Biosynthesis of (−)-(1S,2R)-Allocoronamic Acyl Thioester by an Fe^II-Dependent Halogenase and a Cyclopropane-Forming Flavoprotein

  摘要：

  The biosynthetic gene cluster for the kutzneride family of hexapeptidolactones includes the four-gene cassette ktzABCD postulated to generate a nonproteinogenic amino acid. Encoded by this cassette are the nonheme Fe-II-dependent halogenase KtzD and the acyl-CoA dehydrogenase-like flavoprotein KtzA, proposed to work in conjunction with adenylating protein KtzB and carrier protein KtzC. In the present work, we report the in vitro reconstitution of this four-protein system and identify the final product as (1S,2R)-allocoronamic acid bound in thioester linkage to KtzC. Further analysis of KtzD and KtzA support a biosynthetic pathway that involves KtzD-mediated generation of a y-chloroisoleucyl intermediate which is cyclized to the final product by KtzA without redox participation of the bound flavin cofactor. This work introduces a new monomer for potential incorporation into nonribosomal peptides and validates the unique strategy for its biosynthesis.

  DOI：

  10.1021/ja8064667
• 作为产物：
  描述：

  (4S)-4-benzyl-3-[(2S)-2-(trideuteriomethyl)butanoyl]-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以34%的产率得到
  参考文献：
  名称：

  Biosynthesis of (−)-(1S,2R)-Allocoronamic Acyl Thioester by an Fe^II-Dependent Halogenase and a Cyclopropane-Forming Flavoprotein

  摘要：

  The biosynthetic gene cluster for the kutzneride family of hexapeptidolactones includes the four-gene cassette ktzABCD postulated to generate a nonproteinogenic amino acid. Encoded by this cassette are the nonheme Fe-II-dependent halogenase KtzD and the acyl-CoA dehydrogenase-like flavoprotein KtzA, proposed to work in conjunction with adenylating protein KtzB and carrier protein KtzC. In the present work, we report the in vitro reconstitution of this four-protein system and identify the final product as (1S,2R)-allocoronamic acid bound in thioester linkage to KtzC. Further analysis of KtzD and KtzA support a biosynthetic pathway that involves KtzD-mediated generation of a y-chloroisoleucyl intermediate which is cyclized to the final product by KtzA without redox participation of the bound flavin cofactor. This work introduces a new monomer for potential incorporation into nonribosomal peptides and validates the unique strategy for its biosynthesis.

  DOI：

  10.1021/ja8064667