(S)-2-(methyl-d3)butanal | 1073233-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(methyl-d3)butanal
• CAS: 1073233-01-8
• 化学式: C₅H₁₀O
• 分子量: 89.11
• InChiKey: BYGQBDHUGHBGMD-OJWMFZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 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：
  0.8
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 (S)-2-(methyl-d3)butanal 、 4,4'-二甲氧基二苯甲胺 以 二氯甲烷 为溶剂， 反应 6.0h， 以42 mg的产率得到(3S)-2-((bis(4-methoxyphenyl)methyl)amino)-3-(methyl-d3)pentanenitrile
  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：

  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