(+)-(S)-7-Nitro-1-tetralol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-(S)-7-Nitro-1-tetralol
• 英文别名: (1S)-7-nitro-1,2,3,4-tetrahydronaphthalen-1-ol
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: GTNBTXJNXZBVJP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-硝基-3,4-二氢-2H-1-萘酮 在 N,N-diethylaniline borane 、 硼酸三甲酯 、 chiral 2-(diphenylhydroxymethyl)pyrrolidine 作用下， 以 甲苯 为溶剂， 生成 (+)-(S)-7-Nitro-1-tetralol
  参考文献：
  名称：

  Stereochemical Sensitivity of the Human UDP-glucuronosyltransferases 2B7 and 2B17

  摘要：

  A set of 28 enantiomers comprising rigid and flexible secondary alcohols was synthesized by the asymmetric Corey-Bakshi-Shibata reduction. The enantiomerically pure alcohols were subjected to enzymatic glucuronidation assays employing the human UDP-glucuronosyltransferases (UGTs) 2B7 and 2BI7. Both UGTs displayed high levels of stereo selectivity, favoring the conjugation of the (R)-enantiomers over their respective (S)-stereoisomers at eudismic ratios up to 256. The spatial arrangement of the hydroxy group determined the diastereoselectivity of the UGT2B17-catalyzed reaction in agreement with Pfeiffer's rule (eudismic activity quotient = 0.83 +/- 0.14). Inhibition studies revealed that the enantiomers had similar affinities toward the enzymes. The diastereoselectivity of the UGT-catalyzed conjugation stemmed, therefore, from the arrangement of the substrates in the catalytic site, rather than from distinct affinities toward the enzymes. Taken together, this study showed that metabolic enzymes that are generally conceived to be rather "flexible" in nature are capable of displaying high levels of chiral distinction.

  DOI：

  10.1021/jm051142c

文献信息

• Stereochemical Sensitivity of the Human UDP-glucuronosyltransferases 2B7 and 2B17
  作者：Ingo Bichlmaier、Antti Siiskonen、Moshe Finel、Jari Yli-Kauhaluoma

  DOI：10.1021/jm051142c

  日期：2006.3.1

  A set of 28 enantiomers comprising rigid and flexible secondary alcohols was synthesized by the asymmetric Corey-Bakshi-Shibata reduction. The enantiomerically pure alcohols were subjected to enzymatic glucuronidation assays employing the human UDP-glucuronosyltransferases (UGTs) 2B7 and 2BI7. Both UGTs displayed high levels of stereo selectivity, favoring the conjugation of the (R)-enantiomers over their respective (S)-stereoisomers at eudismic ratios up to 256. The spatial arrangement of the hydroxy group determined the diastereoselectivity of the UGT2B17-catalyzed reaction in agreement with Pfeiffer's rule (eudismic activity quotient = 0.83 +/- 0.14). Inhibition studies revealed that the enantiomers had similar affinities toward the enzymes. The diastereoselectivity of the UGT-catalyzed conjugation stemmed, therefore, from the arrangement of the substrates in the catalytic site, rather than from distinct affinities toward the enzymes. Taken together, this study showed that metabolic enzymes that are generally conceived to be rather "flexible" in nature are capable of displaying high levels of chiral distinction.