Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry

International Research Journal of Pure and Applied Chemistry Pub Date : 2023-09-22 DOI:10.9734/irjpac/2023/v24i5830

João Rufino de Freitas Filho, Jucleiton José Rufino de Freitas, Pedro Ramos de Souza Neto, Fabrícia Aparecida Marques de Souza, Adiel Soares Ferreira, Anne Gabrielle Marques da Silva, Francisco Antonio Mabson Henrique Lopes, Marcilio Martins de Moraes, Clécio Souza Ramos, Ronaldo Nascimentos de Oliveira

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Abstract

The anomeric effect in carbohydrate chemistry is known as the interaction between the OHd substituent at the anomeric position to favor an axial orientation rather than an equatorial one, despite the increased 1,3-diaxial interactions. In the anomeric effect, a sugar ring is stabilized by an electronegative substituent at the C1 carbon, also known as the anomeric carbon. The stabilization is thought to result from interactions between lone electron pairs on oxygen and a C1 antibonding orbital. On the other hand, the anomeric effect can be of two types: endo-anomeric and exo-anomeric. The effect is called endo-anomeric when the lone pair comes from the oxygen atom in the sugar ring and exo-anomeric when the lone pair comes from oxygen in a substituent on C1. Several factors influence the anomeric effect. In this way, this review aims to describe the recent advances in main theories, observations, and advances achieved in the last decades related to the anomeric effect. GRAPHICAL ABSTRACT

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碳水化合物化学中异头和异头效应的研究进展

在碳水化合物化学中，尽管1,3-二轴相互作用增加，但羟基取代基之间的相互作用使其倾向于轴向而不是平伏方向，这就是羟基取代基之间的相互作用。在异头效应中，糖环被C1碳(也称为异头碳)上的电负性取代基稳定。稳定被认为是由于氧上的孤电子对和C1反键轨道之间的相互作用。另一方面，这种效应可以分为内、外两种类型。当孤对来自糖环上的氧原子时，这种效应被称为内端异构;当孤对来自C1上取代基上的氧时，这种效应被称为外端异构。影响球头效应的因素有几个。通过这种方式，本文旨在描述最近几十年来与反常效应有关的主要理论、观测和进展的最新进展。图形抽象# x0D;

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International Research Journal of Pure and Applied Chemistry

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