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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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使用Issatchenkia orientalis生产高产量的3-基酸.

Shih-I Tan1,2,3, Sarang S Bhagwat2,3,4, Teresa A Martin1,2,3

  • 1Department of Chemical and Biomolecular Engineering, University of Illinois Urbana-Champaign, Urbana, IL, USA.

Nature communications
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概括

我们设计了Issatchenkia orientalis酵母,以可持续生产3-Hydroxypropionic acid (3HP),这是一个关键的生物塑料前体. 这种耐酸酵母可以实现高产量,使生物制造具有成本效益.

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科学领域:

  • 生物技术是生物技术.
  • 代谢工程是代谢工程.
  • 工业微生物学 工业微生物学

背景情况:

  • 生物制造为传统化学生产提供了一个可持续的替代方案.
  • 3-基酸 (3HP) 是一种高价值的化学物质和生物塑料的前体,但具有成本效益的微生物生产具有挑战性.
  • 东方酵母是一种耐酸酵母,具有低pH生物工艺的潜力.

研究的目的:

  • 为了建立Issatchenkia orientalis作为一个强大的宿主,用于低pH的3-Hydroxypropionic酸 (3HP) 生合成.
  • 识别和优化代谢途径,以实现高效的3HP生产.
  • 为了评估使用这种工程酵母的3HP生产的经济可行性.

主要方法:

  • 基因组规模建模以确定最佳生物合成途径 (β-氨酸途径).
  • 序列相似性网络分析以发现高活性酶 (PAND,BAPAT,YDFG).
  • 代谢工程策略包括基因整合,基因淘汰和基因过度表达.
  • 使用低成本介质 (玉米液) 在受控的pH值下进行料批发发酵.

主要成果:

  • 确定β-氨酸途径是3HP生产的最佳途径.
  • 工程I. orientalis在摇瓶中达到29 g/L的标位,在料批发发酵中达到92 g/L的标位.
  • 在pH4.0下获得高产量 (0.7g/g) 和生产率 (0.55g/L/h).
  • 技术经济分析表明,在经济上可行的烯酸生产的潜力.

结论:

  • 东方卫星 (Issatchenkia orientalis) 是一个有前途的平台,用于成本效益高的3HP生产.
  • 优化的代谢工程和发酵条件显著提高了3HP的产量.
  • 这项工作支持可持续生物塑料前体的工业商业化.