Polysaccharides as separation media for the separation of proteins, peptides and stereoisomers of amino acids

Fan, Xiaojun; Cao, Lilong; Geng, Linna; Ma, Yalu; Wei, Yuping; Wang, Yong

doi:10.1016/j.ijbiomac.2021.07.032

Cited by 14 publications

(7 citation statements)

References 251 publications

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“…The results showed that large molecular dyes, such as methylene blue, methyl orange, and rhodamine B, could diffuse throughout Zr-HMOFs 1 – 3 uniformly, suggesting the accessibility of large substrates into the porous frameworks of these materials in solution. In view of the structural characteristics of these Zr-HMOF materials (such as chirality, large cage enclosed by terphenyls, and flexible chiral amine alcohol pendants protruding into the cages), Fmoc- L / D -AAs (important precursor compounds in the manufacturing of therapeutic peptides) were selected as the chiral resolution substrates to investigate the enantioselective adsorption performance of our Zr-HMOF materials. Very interestingly, Zr-HMOFs 1 – 3 were prepared with the same chiral and hydrogen-bonding sites but slightly different π-binding sites.…”

Section: Resultsmentioning

confidence: 99%

Engineering UiO-68-Typed Homochiral Metal–Organic Frameworks for the Enantiomeric Separation of Fmoc-AAs and Mechanism Study

Yuan

et al. 2023

ACS Appl. Mater. Interfaces

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Homochiral metal−organic frameworks (HMOFs) have been widely investigated in the application of enantiomeric separation. Nonetheless, it remains a significant challenge to explore the effect of multiple weak interactions between HMOF adsorbents and chiral adsorbates on enantiomeric separation performance still. In this work, robust chiral amine-alcohol-functionalized UiO-68-typed Zr-HMOFs 1−3 with the same hydrogen-bonding sites but slightly different π-binding sites were prepared for the enantioseparation of amino acid derivatives (Fmoc-AAs) with large πbinding groups. As a consequence of multiple host−guest interactions, these Zr-HMOFs exhibit speedy adsorption and high adsorption capacity for Fmoc-L/D-AAs and dissimilar enantioselectivity for the adsorption of their enantiomers. Materials 1 and 2 exhibit excellent enantioselective separation performance for Fmoc-valine with a single terminal π-binding group, while material 3 displays excellent enantioselective separation performance for Fmoc-phenylalanine and Fmoc-tryptophan with π-binding groups at both ends. As evidently demonstrated by our experimental and density functional theory (DFT) computational results, when the number of π-binding groups preset in the confined chiral space of adsorbents matches the number of π-binding groups of chiral adsorbates, the synergism of π−π or σ−π interactions will increase enantioselectivity; otherwise, the competition interactions from redundant identical binding sites will weaken enantioselectivity. Our case not only provides a tremendously typical system for investigating the collaborative discrimination of multiple weak interactions and exploring the impact of relatively excessive binding sites of HMOF adsorbents or chiral adsorbates on the enantioselective separation performance but also provides guidance for targeted functional modifications of high-performance chiral porous materials.

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Section: Resultsmentioning

confidence: 99%

Engineering UiO-68-Typed Homochiral Metal–Organic Frameworks for the Enantiomeric Separation of Fmoc-AAs and Mechanism Study

Yuan

et al. 2023

ACS Appl. Mater. Interfaces

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“…Within a single strand of the amylose tris(3,5‐dimethylphenylcarbamate) selector, interactions with solute occurred in various ways via π‐π interactions and hydrogen bonds. For some molecules, for example, naringenin the authors also noted interactions of the molecule with two adjacent amylose strands [62]. In this study, dimerization of naringenin was also observed, but the authors stressed that they used a high concentration of the analyte during their modeling procedure to speed up the computational process so that a dimerization appears to be unlikely to take place under dilution conditions such as the chromatographic process.…”

Section: Chiral Selectorsmentioning

confidence: 86%

“…For summaries of general features of polysaccharide-based chiral selectors see, for example [14][15][16][17][18][19][20][21]23]. Molecular modeling approaches have been summarized recently [58][59][60][61] as have applications of polysaccharide CSPs to the enantioseparations [62,63] or the preparation of polysaccharide selectors [63,64]. Depending on the derivatization, the cellulose or amylose CSPs differ in size and shape of the chiral grooves [19,65].…”

Section: Polysaccharidesmentioning

confidence: 99%

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Update on chiral recognition mechanisms in separation science

Scriba

2024

J of Separation Science

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The stereospecific analysis of chiral molecules is an important issue in many scientific fields. In separation sciences, this is achieved via the formation of transient diastereomeric complexes between a chiral selector and the selectand enantiomers driven by molecular interactions including electrostatic, ion‐dipole, dipole‐dipole, van der Waals or π‐π interactions as well as hydrogen or halogen bonds depending on the nature of selector and selectand. Nuclear magnetic resonance spectroscopy and molecular modeling methods are currently the most frequently applied techniques to understand the selector‐selectand interactions at a molecular level and to draw conclusions on the chiral separation mechanism. The present short review summarizes some of the recent achievements for the understanding of the chiral recognition of the most important chiral selectors combining separation techniques with molecular modeling and/or spectroscopic techniques dating between 2020 and early 2024. The selectors include polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, donor‐acceptor type selectors, ion‐exchangers, crown ethers, and molecular micelles. The application of chiral ionic liquids and chiral deep eutectic solvents, as well as further selectors, are also briefly addressed. A compilation of all published literature on chiral selectors has not been attempted.

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“…It is essential to investigate a sensitive and efficient approach for enantiorecognizing AAs enantiomers. [122][123][124][125][126] In addition to Cu-Pt NPs, CdTe QDs were modified with L-Cys for the chiral recognition of Tyr enantiomers. 127 Results also suggested different interactions of L-and D-Tyr with L-Cys/CdTe QDs.…”

Section: Creating a Cooperative Relationship Between Proteins And Nan...mentioning

confidence: 99%

A cooperation tale of biomolecules and nanomaterials in nanoscale chiral sensing and separation

Hong,

Zhou,

Tan

et al. 2023

Nanoscale Horiz.

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Polysaccharides as separation media for the separation of proteins, peptides and stereoisomers of amino acids

Cited by 14 publications

References 251 publications

Engineering UiO-68-Typed Homochiral Metal–Organic Frameworks for the Enantiomeric Separation of Fmoc-AAs and Mechanism Study

Engineering UiO-68-Typed Homochiral Metal–Organic Frameworks for the Enantiomeric Separation of Fmoc-AAs and Mechanism Study

Update on chiral recognition mechanisms in separation science

A cooperation tale of biomolecules and nanomaterials in nanoscale chiral sensing and separation

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