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相关概念视频

Oligosaccharide Assembly01:24

Oligosaccharide Assembly

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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
Multiple sugar molecules that may or may...
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Protein Glycosylation

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Glycosylation, the most common post-translational modification for proteins, serves diverse functions. Adding sugars to proteins makes the proteins more resistant to proteolytic digestion. Glycosylated proteins can act as markers and receptors to promote cell-cell adhesion. Additionally, they have many essential quality control functions in the cell, such as correct protein folding and facilitating transport of misfolded proteins to the cytosol, which can be degraded.
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Naming Enantiomers02:21

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

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As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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  1. 首页
  2. 碳水化合物的选择性轴向赤道表皮化
  1. 首页
  2. 碳水化合物的选择性轴向赤道表皮化

相关实验视频

Sequencing of Plant Wall Heteroxylans Using Enzymic, Chemical Methylation and Physical Mass Spectrometry, Nuclear Magnetic Resonance Techniques
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Sequencing of Plant Wall Heteroxylans Using Enzymic, Chemical Methylation and Physical Mass Spectrometry, Nuclear Magnetic Resonance Techniques

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碳水化合物的选择性轴向赤道表皮化

Hayden M Carder1, Yong Wang1, Alison E Wendlandt1

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|June 22, 2022

在PubMed 上查看摘要

概括
此摘要是机器生成的。

这项研究引入了糖异构的基质介导方法,将常见的甘氨酸转化为罕见的异构体. 这种高效的工艺可以合成多种不同且不自然的糖结构.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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科学领域:

  • 碳水化合物化学
  • 有机合成
  • 激进化学

背景情况:

  • 在合成复杂碳水化合物方面,基质转化是有价值的.
  • 现有的糖异构化方法存在局限性.
  • 需要有效的方法来获取罕见的糖异构体.

研究的目的:

  • 开发一种新的基质介导方法,用于在糖中进行轴向到赤道的酒精表皮化.
  • 将丰富的甘氨酸转化为具有高选择性的稀有异构体.
  • 为了证明这种异构化对糖合成和多样化的合成实用性.

主要方法:

  • 使用激素介导反应进行选择性酒精表皮化.
  • 使用α-基C-H键的H原子抽象进行立体控制.
  • 研究位点和异位选择性的机制方面.

主要成果:

  • 建立了一个高度可预测和选择性的基质介导糖异构化方法.
  • 该方法有效地将丰富的甘氨酸转化为稀有异构体.
  • 已证明在有效的甘氨酸合成和单步甘氨酸多样化中具有成功的应用.
  • 机理学研究阐明了H原子抽象在实现选择性的作用.

结论:

  • 开发的基质介导表皮化是获取罕见糖异构体的强大工具.
  • 这种方法提供了对现有的糖异构化技术的补充反应性.
  • 这种方法促进了高效的甘氨酸合成和多样化,扩大了对非自然碳水化合物结构的获取.