Hai Dong

Huazhong University of Science and Technology

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Zhichao Pei

Northwest A&F University

Olof Ramström

University of Massachusetts Lowell

Bo Ren

Xinxiang University

Jiantao Ge

Huazhong University of Science and Technology

Yang‐Fan Guo

Huazhong University of Science and Technology

Yixuan Zhou

Guangdong Pharmaceutical University

Jian Lv

Qingdao University of Science and Technology

Yuxin Pei

Northwest A&F University

Tao Luo

Central South University

Yuchao Lu

Changzhi Medical College

Cooperative Institutions

Huazhong University of Science and Technology

Chinese Academy of Sciences

Novartis (China)

KTH Royal Institute of Technology

Northwest A&F University

Novartis (Switzerland)

Dalian University of Technology

Tianjin University

Jilin University

Sichuan University

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Oriented and reversible immobilization of His-tagged proteins on two- and three-dimensional surfaces for study of protein–protein interactions by a QCM biosensor

Sensors and Actuators B Chemical (2015)

Xueming Li Siyu Song Yuxin Pei Hai Dong Teodor Aastrup

Quartz Crystal Microbalance

Surface protein

Protein crystallization

10.1016/j.snb.2015.10.096

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Citations (20)

Regioselective Glycosylation of Mannoside and Galactoside Acceptors Containing 2,4-OH Achieved by Altering Protecting Groups at the 1,3,6-Positions

The Journal of Organic Chemistry (2024)

Yang‐Fan Guo Jiancheng Yu Hai Dong

In this study, we systematically investigated the regioselective glycosylation of 2,4-OH mannoside and galactoside acceptors since regioselective protection of their 3- and 6-OHs is readily achieved. By altering the protecting groups at 1-, 3-, and 6-positions of such acceptors, we finally screened p-methoxyphenyl 3-OBn, 6-OTBDPS, α-mannoside, and β-galactoside acceptors whose 2-OHs exhibited excellent selectivity for glycosylation with various glycosyl donors, leading to 1,2-linked products in 70–82% yields. By utilizing such acceptors, a series of 2,4-linked trisaccharide products (53–65% yields over two steps) have been highly efficiently synthesized without the need for complex protection/deprotection operations at the 2- and 4-positions of these acceptors.

Trisaccharide

Galactosides

Protecting group

10.1021/acs.joc.4c00618

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Metal-Assisted Multiple-Crosslinked Thin Film Composite Hollow Fiber Membrane for Highly Efficient Bioethanol Purification

SSRN Electronic Journal (2022)

Tengyang Zhu Shutong Liu Qing Xia Ming Yi Huan Liu

Polyamide-based thin film composite (TFC) membranes have been extensively applied in various membrane-based separations. However, research works for bioethanol purification are relatively limited due to insufficient hydrophilicity and chain packing density of the polyamide selective layer by conventional interfacial polymerization. In this work, a new TFC hollow fiber (HF) membrane is fabricated by metal-assisted multiple crosslinking strategy, that is, metal-coordinated crosslinking of the pristine polyamide layer and coordination complexation between metal ions and phytic acid (PA) for advanced water/ethanol separation. By tuning coordination abilities of metal ions with polyamide and PA and the cycle number of PA/metal ion assembly, polyamide-based TFC HF membrane is perfected. Additionally, a joint experiment/simulation characterization is deployed to reveal the coordination abilities of various metal ions with the pristine polyamide and grafted PA. Ultimately, the synergistic effect between polyamide layer and PA-metal ion complexes (i.e., 1+1 > 2 effect) is embodied in the separation performance of water/ethanol separation. The resulting TFC-Fe 3+ -PA membrane with the strongest PA-metal ion coordination ability exhibits the best water/ethanol separation performance, i.e., the separation factor of 1703 (34 times higher than pristine polyamide TFC HF membrane) and total flux of 1705 g/m 2 h. This metal-assisted multiple crosslinking strategy is therefore believed to shed important lights on the development of next-generation high-performance TFC membranes for bioethanol purification.

Thin-film composite membrane

Interfacial polymerization

10.2139/ssrn.4098282

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Citations (3)

S-Acetyl migration in synthesis of sulfur-containing glycosides

Tetrahedron (2014)

Yixuan Zhou Xiaoling Zhang Bo Ren Bin Wu Zhichao Pei

Leaving group

10.1016/j.tet.2014.07.014

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Citations (19)

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

Chemistry - A European Journal (2016)

Bo Ren Olof Ramström Qiang Zhang Jiantao Ge Hai Dong

Abstract In this study, [Fe(dibm) 3 ] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2‐ and 1,3‐diol‐containing structures. The mechanism is proposed to proceed via a cyclic dioxolane‐type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition‐metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

10.1002/chem.201504477

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Citations (48)

SnCl₂‐Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

European Journal of Organic Chemistry (2022)

Jian Lv Chunyang Liu Yang‐Fan Guo Guang‐Jing Feng Hai Dong

Abstract Based on SnCl 2 ‐catalyzed acetalation and selective benzoylation, a one‐pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2‐OH/3‐OH was developed. Consequently, 2‐OBz or 3‐OBz 4,6‐ O ‐benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.

Galactosides

Sequence (biology)

10.1002/ejoc.202101565

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Citations (9)

Enhanced Basicity by Supramolecular Anion Activation

Hai Dong Olof Ramström

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study, the effects of the neighboring group on the Lattrell-Dax inversion were explored. A new carbohydrate/anion host-guest system was discovered and the ambident reactivity of the nitrite anion was found to cause a complicated behavior of the reaction. It has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, restricting the nitrite N-attack, thus resulting in O-attack only and inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed by use of double parallel and double serial inversion. A supramolecularly activated, triggered cascade reaction was also developed. This cascade reaction is triggered by a deprotonation process that is activated by anions. It was found that the anions can activate this reaction following their hydrogen bonding tendencies to the hydroxyl group in aprotic solvents.

Reactivity

Epimer

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Solvent-Dependent, Kinetically Controlled Stereoselective Synthesis of 3- and 4-Thioglycosides

The Journal of Organic Chemistry (2005)

Zhichao Pei Hai Dong Olof Ramström

Facile approaches to prepare 3- and 4-thioglycosides of the galacto, gulo, and gluco type from the parent triflates are presented. The dependencies of the solvent and the protecting group pattern, as well as the configuration of the neighboring and leaving groups, have been studied for these reactions. The results clearly show that the efficient stereoselective synthesis of methyl 3-thio-galactoside depends highly on the solvent and the nucleophile concentration.

Thio-

Protecting group

10.1021/jo050650r

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Citations (17)

Regio/Site-Selective Benzoylation of Carbohydrates by Catalytic Amounts of FeCl₃

ACS Omega (2018)

Jian Lv Tao Luo Ying Zhang Zhichao Pei Hai Dong

This work uncovered the regio/site-selective benzoylation of 1,2- and 1,3-diols and glycosides containing a cis-vicinal diol using a catalytic amount of FeCl3 with the assistance of acetylacetone. FeCl3 may initially form [Fe(acac)3] (acac = acetylacetonate) with excess acetylacetone in the presence of diisopropylethylamine (DIPEA) in acetonitrile at room temperature. Then, benzoylation was catalyzed by Fe(acac)3 with added benzoyl chloride in the presence of DIPEA under mild conditions as reported. This reaction produced selectivities and isolated yields similar to or slightly lower than the reaction using Fe(acac)3 as a catalyst in most cases. The result provides not only the green and convenient selective benzoylation method associated with the most inexpensive catalysts but also the possibility that the effects of various metal salts and ligands on the regioselective protection can be extensively investigated in future study to obtain the optimized catalytic system.

Acetylacetone

10.1021/acsomega.8b02360

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Citations (20)

Copper(i)-catalyzed radical decarboxylative imidation of carboxylic acids with N-fluoroarylsulfonimides

Chemical Communications (2016)

Zhongxue Fang Yu Feng Hai Dong Dashan Li Tiandi Tang

An efficient copper-catalyzed radical decarboxylative imidation reaction is presented.

Decarboxylation

10.1039/c6cc03227c

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Citations (34)