(R)-6-oxo-4-((2R,3S)-3,5,7-trihydroxychroman-2-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid | 1245030-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-6-oxo-4-((2R,3S)-3,5,7-trihydroxychroman-2-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid
• CAS: 1245030-11-8
• 化学式: C₁₅H₁₄O₈
• 分子量: 322.271
• InChiKey: OUINRAMXVOPMLQ-ZKYQVNSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  133.52
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  儿茶提取物 在 cell suspensions of culture of Cylindrocarpon radicicola ATCC 11011 (C_. radicicola ATCC 11011) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以14 mg的产率得到(S)-6-oxo-4-((2R,3S)-3,5,7-trihydroxychroman-2-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  （+）儿茶素到新型B环裂变内酯的生物转化

  摘要：

  Thirty-six microorganisms were screened for their abilities to transform (+)-catechin to metabolites. Of these, Aspergillus giganteus UI 10, A. ochraceous ATCC 1008, Cylindrocarpon radicicola ATCC 11011, Amycolata autotrophica ATCC 35203, Mycobacterium flavescens ATCC 14474, M. fortuitum UI 53378, Streptomyces rimosus NRRL 2234, S. griseolus ATCC 11796, and S. griseus ATCC 13273, converted (+)-catechin to new products. C. radicicola and S. griseolus were chosen for preparative-scale incubations to produce polar products, which were isolated and characterized by UV, NMR, and mass spectral analyses. The products were new carboxylic acid lactones formed by B-ring fission of catechin. Labeling with O-18(2) showed incorporation of two oxygen atoms into the new lactone products. Based on O-18(2) labeling, likely pathways for lactone formation involved initial dioxygenase-mediated meta B-ring cleavage followed either by aldehyde oxidation to a diacid that lactonizes, or by hemiacetal (lactal) formation followed by alcohol oxidation. We believe this to be the first example of microbial B-aryl-ring cleavage in catechins.

  DOI：

  10.1021/op100108j