2-(6-methoxy-naphthalen-2-yl)-propionic acid 2-methoxy-ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(6-methoxy-naphthalen-2-yl)-propionic acid 2-methoxy-ethyl ester
• 英文别名: 2-methoxyethyl (2R)-2-(6-methoxynaphthalen-2-yl)propanoate
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: MQRQYOJNRZXCSE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 whole cells of Trichosporon sp 作用下， 以 phosphate buffer 为溶剂， 反应 96.0h， 生成 萘普生 、 (R)-萘普生 、 (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid 2-methoxy-ethyl ester 、 2-(6-methoxy-naphthalen-2-yl)-propionic acid 2-methoxy-ethyl ester
  参考文献：
  名称：

  Enzymatic resolution of naproxen

  摘要：

  Trichosporon sp. (TSL), a newly found strain isolated from a locally fermented cottage cheese has been found to be highly stereoselective in the resolution of (S)-(+)-naproxen (ee >99%, Esimilar to500) from the corresponding racemic methyl ester. The process of resolution using whole cells has been scaled up to multi-kg level. Optimization of experimental conditions including downstream processing at 80-100 g/L substrate concentration with >90% recovery has been achieved. Changes in the physical parameters such as the particle size of the substrate play an important role in the resolution kinetics. A new strain of Trichosporon sp. having high cell density in cultivation (>60 g dry cell mass L-1 in 14-16 h) is found to be sufficiently stable for two years in dry powder form at 5-8degreesC. The viability of the resolution process has been further improved by the development of a simple racemization process for the enriched (R)-(-)-ester. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00492-0

文献信息

• Enzymatic resolution of naproxen
  作者：Surrinder Koul、Rajinder Parshad、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/s0957-4166(03)00492-0

  日期：2003.8

  Trichosporon sp. (TSL), a newly found strain isolated from a locally fermented cottage cheese has been found to be highly stereoselective in the resolution of (S)-(+)-naproxen (ee >99%, Esimilar to500) from the corresponding racemic methyl ester. The process of resolution using whole cells has been scaled up to multi-kg level. Optimization of experimental conditions including downstream processing at 80-100 g/L substrate concentration with >90% recovery has been achieved. Changes in the physical parameters such as the particle size of the substrate play an important role in the resolution kinetics. A new strain of Trichosporon sp. having high cell density in cultivation (>60 g dry cell mass L-1 in 14-16 h) is found to be sufficiently stable for two years in dry powder form at 5-8degreesC. The viability of the resolution process has been further improved by the development of a simple racemization process for the enriched (R)-(-)-ester. (C) 2003 Elsevier Ltd. All rights reserved.