Absolute Configuration Determination of Sugar: A Review of the Different Methods

João Rufino de Freitas Filho, J. C. R. Freitas, Juliano Carlo Rufino Freitas, M. Belian, Claudio Augusto Gomes da Camara, Pedro Ramos de Souza Neto, Alécia Regina Andresa Silva, Alex Sandro Nascimento da Silva Filho, Alice Mariana Souza de Almeida, Jonatas Tavares da Silva, Mirian Luzinete da Silva, Anne Gabrielle Marques da Silva, Marcilio Martins de Moraes, Clécio Souza Ramos, Ronaldo Nascimentos de Oliveira
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Abstract

Determination of the stereochemistry of the stereocenter from the aglyconic part of carbohydrates is always one of the most important tasks for chemistry carbohydrates researchers. The absolute configuration (AC), a challenge for synthetic chemists, has attracted much attention. During the past few decades, many techniques and approaches have been developed to determine the AC of carbohydrates, including methods of X-ray diffraction (XRD), electronic and vibrational circular dichroism (ECD and VCD), Raman optical activity (ROA), nuclear magnetic resonance (NMR) utilizing anisotropic effects of chiral derivatizing agents, and quantum chemical calculations. On the other hand, none of the currently applied techniques can dominate AC determination, since they each have their respective limitations corresponding to the different structural features. This review summarizes most of the techniques and methods commonly used in AC assignment of carbohydrates (but specifically glycosides), in the last decades (2000-2023). GRAPHICAL ABSTRACT
糖的绝对构型测定:不同方法综述
从碳水化合物的缩醛部分确定立体中心的立体化学结构一直是碳水化合物化学研究人员最重要的任务之一。绝对构型(AC)是合成化学家面临的一项挑战,备受关注。在过去的几十年里,人们开发了许多技术和方法来确定碳水化合物的绝对构型,包括 X 射线衍射(XRD)、电子和振动圆二色性(ECD 和 VCD)、拉曼光谱(ROA)、利用手性衍生剂各向异性效应的核磁共振(NMR)以及量子化学计算等方法。另一方面,目前应用的所有技术都无法主导交流电测定,因为它们都有各自的局限性,与不同的结构特征相对应。本综述总结了过去几十年(2000-2023 年)在碳水化合物(特别是苷类)AC 定义中常用的大多数技术和方法。图表摘要
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