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Chinese Chemical Letters 2024年第5期35卷 155-160页

作者： Shuying Li Weiwei ZhuGe Xuan Sun Chongzhen Sun Zhaojun Liu Chenghe Xiong Min Xiao Guofeng Gu national glycoengineering research center and shandong key laboratory of carbohydrate chemistry and glycobiology Shandong UniversityQingdao 266237China NMPA key laboratory for Quality research and Evaluation of carbohydrate-based Medicine Shandong UniversityQingdao 266237China

The galactomannan from Antrodia cinnamomea(AC)is characterized as one of the important bioactive components that exhibits potential immunostimulatory *** biological function of its corresponding oligosaccharide fragments has not been revealed *** this study,we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation *** preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation,phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro,indicating its immense potential as an immunostimulant candidate.

关键词： Antrodia cinnamomea Galactomannan Oligosaccharide Immunostimulatory propriety Chemical synthesis

Concise Synthesis of Lactococcus garvieae Lipoteichoic Acids Through an Additive-Modulated Preactivation Protocol and the Immunological Studies

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CCS chemistry 2024年第2期6卷 403-414页

作者： Tianlu Li Tong Li Yue Yang Haoru Zhuang Jianwu Lv Ning Zhou Miaomiao Zhang Fengshan Wang Yiqun Geng Richard R.Schmidt Peng Peng national glycoengineering research center Shandong Key Laboratory of Carbohydrate Chemistry and GlycobiologyNMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate Based MedicineShandong UniversityQingdao 266237 State key laboratory of Bioactive Substance and Function of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050 Department of chemistry University of KonstanzD-78457 Konstanz

Lipoteichoic acids(LTAs)are macroamphiphiles composed of alditol,lipid,phosphate,and carbohydrate *** to their inherent complexity,it is a severe challenge to access LTAs with structural integrity from natural sources for biological or immunological ***,we describe the first total synthesis of Lactococcus garvieae LTA(type II LTA),containing five distinct 1,2-cis gluco/galactopyranosidic linkages,via a novel additive-modulated O-glycosyl trichloroacetimidate preactivation glycosidation *** strategy features(1)high glycosidation yields and excellent 1,2-cis stereoselectivities independent of the donor anomeric configuration,(2)common and inexpensive reagents as promoters and additives,(3)application to standard glycosyl imidate donors without resorting to participating protection,and(4)general application to reactive and less reactive glycosyl ***,via the precise stereocontrolled construction of three galactopyranosidic and two glucopyranosidic bonds on a multigram scale,a series of structurally well-defined LTA molecules were successfully *** evaluation of these type II synthetic LTAs showed a structure–activity relationship in the stimulation of a proinflammatory response.

关键词： 1,2-cis glycosidation stereoselectivity lipoteichoic acid total synthesis additive-modulated trichloroacetimidate glycosidation immune response

Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis

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Science China chemistry 2021年第4期64卷 552-557页

作者： Xiaoxiao Yan Feng Feng Lin Zhou Linrong Chen Shouchu Tang Jian Liu Feng Cai Xiaolei Wang State key laboratory of Applied Organic chemistry Department of Chemistry and School of PharmacyLanzhou UniversityLanzhou 730000China The national glycoengineering research center and shandong Provincial key laboratory of carbohydrate chemistry and glycobiology Shandong UniversityQingdao 266237China

Herein,we reported the stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis and found a suitable system to resolve many challenges,such as the tolerance towards the density of functional groups,the variability of the anomeric position,the compatibility of appropriate catalyst combinations,the regioselectivity of nucleophiles,and the match/mismatch problems between chiral substrates and chiral ligand-metal *** method enables the efficient preparation of a series of unnatural C-glycosamino acid skeletons bearing two contiguous stereogenic centers in good yields with excellent *** this crucial precursor,various C-glycosamino acid derivatives have been achieved *** readily prepared C-glycosamino acid hybrids will meet the growing demands for the development of new molecular entities for discovering new drugs and *** stereodivergent synthesis of C-glycosamino acids will further accelerate the study of their structural features,mode of action,and potential biological applications in the near future.

关键词： C-glycosamino acid glycomimetics peptidomimetics stereodivergent dual catalysis

Chemical Synthesis of an Octasaccharide Derivative Related to Group B Streptococcus Cell-Wall Polysaccharide

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Chinese Journal of chemistry 2023年第2期41卷 151-158页

作者： Chongzhen Sun Zhaojun Liu Wuxian Zeng Xiaolin Ma Guirong Wang Guofeng Gu national glycoengineering research center and shandong Provincial key laboratory of carbohydrate chemistry and glycobiology Shandong University72 Binhai RoadQingdaoShandong 266237China NMPA key laboratory for Quality research and Evaluation of carbohydrate-based Medicine Shandong University72 Binhai RoadQingdaoShandong 266237China

Group B Streptococcus(GBS)is the major pathogen that causes invasive infectious diseases in neonates and *** develop-ment of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject *** B carbohydrate(GBC),the group B-specific polysaccharide that distinguishes GBS with other streptococci species,has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra-antennary *** this paper,a highly convergent[3+5]glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligo-saccharide unitⅡhas been *** this synthesis,each glycosylation reaction was efficiently constructed with glycosyl im-idates,especially trifluoroacetimidate,as donors,and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2-O-position of imidate donors or the solvent effect of Et_(2)***,the ami-noethylphosphate group was smoothly installed on the 6-O-position of D-glucitoll residue using the phosphoramidite *** global deprotection,the target octasaccharide was successfully obtained from o-glucitol in 29 steps with an overall yield of 1.37%.The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functional-ized biomolecules for further biological studies.

关键词： carbohydrate Oligosaccharide Glycosylation Chemical synthesis Group B carbohydrate

Stereodirecting Effects of 4-O-ortho-cyanobenzyl Ether on Chemical Glycosylation with Glucopyranosyl Donor

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Chinese Journal of chemistry 2023年第6期41卷 651-656页

作者： Han Zhang Aoxin Guo Youhui Meng Yue Wang Jian Gao Xue-Wei Liu national glycoengineering research center shandong key laboratory of carbohydrate chemistry and glycobiology NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based MedicineShandong UniversityQingdaoShandong 266237China Division of chemistry and Biological chemistry School of Physical and Mathematical SciencesNanyang Technological University 21NanyangLinkSingapore 637371Singapore

Here we report a systematic investigation on the stereodirecting effects of a 4-O-ortho-cyanobenzyl ether(oBCN)group with a glucopyranosyi *** studies revealed that the glycosylation reactions using this donor generally show dual-stereoselectivities depending on the acceptor nucleophilicity,that is,glycosylation of weak nucleophile acceptors generally affordsα-glycosides specifically while glycosylation of strong nucleophile acceptors affords β-glycosides preferentially.

关键词： Glycosylation Oligosaccharides Diastereoselectivity Cyanobenzyl ether Hydrogen bonds

Recent Advances in Glycopeptide and Glycoprotein Synthesis:A Refined Synthetic Probe towards the Biological World

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Chinese Journal of chemistry 2023年第16期41卷 2010-2024页

作者： Haoru Zhuang Huiran Hao Yongshun Qiu Jinjuan Gan Tianlu Li Shenzhen research Institute of shandong University A301 Virtuol University Park in South District of ShenzhenShenzhenGuangdong 518057China Notional glycoengineering research center Shandong Key Laboratory of Carbohydrate Chemistry and GlycobiologyNMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate Based MedicineShandong UniversityQingdaoShandong 266237China

Comprehensive Summary Protein glycosylation is the most complex and diverse form of post-translational modification in human ***,glycosylation of peptides and proteins emerges as a promising strategy to improve the pharmacokinetic profile of peptide-and protein-based *** to the importance of protein glycosylation,a rigorous evaluation of the relationship between the precise structure and biological function of glycoproteins has to be ***,chemical synthesis,chemoenzymatic synthesis and semisynthesis strategies have attracted extensive attentions towards the preparation of structurally defined glycopeptides and glycoproteins;the obtained synthetic glycoforms thus enable the thorough investigation of specific effects of protein glycosylation.

关键词： Glycoproteins Glycopeptides Glycosylation Total synthesis Biosynthesis Structure-activity relationships

Sequential One-Pot Three-Enzyme Synthesis of the Tetrasaccharide Repeating Unit of Group B Streptococcus Serotype Ⅷ Capsular Polysaccharide

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Chinese Journal of chemistry 2022年第9期40卷 1039-1044页

作者： Min Liang Wei Gong Chongzhen Sun Jielin Zhao Hong Wang Zonggang Chen Min Xiao Guofeng Gu national glycoengineering research center Shandong Provincial Key Laboratory of Carbohydrate Chemistry and GlycobiologyShandong University72 Binhai RoadQingdaoShandong 266237China School of Pharmaceutical Science Shandong University44 West Wenhua RoadJinanShandong 250012China NMPA key laboratory for Quality research and Evaluation of carbohydrate-based Medicine Shandong UniversityQingdaoShandong 266237china

The biochemical property and functional identification of three recombinant glycosyltransferases,includingβ-1,4-rhamnosyltransferase(Cps8R),β-1,4-galactosyltransferase(Cps8) and α-2,3-sialyltransferase(Cps8K)involved in the biosynthesis of the tetrasaccharide repeating unit of serotypeⅧcapsular polysaccharide(CPS)of Group B Streptococci(GBS),were systematically ***,these recombinant enzymes were employed for one-pot three-enzyme efficient synthesis of the tetrasaccharide repeating unit of GBS serotypeⅧCPS using the chemically synthesized Glca-PP-(CH2)ir-OPh as the starting substrate in a satisfying yieldof 87%.

关键词： Streptococcus agalactiae Capsular polysaccharide Oligosaccharides Enzyme catalysis Biosynthesis

Stereoselective synthesis of the 3,6-branched Fuziα-glucans up to 15-mer via a one-pot and convergent glycosylation strategy

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Chinese Chemical Letters 2023年第6期34卷 341-345页

作者： Qingpeng Zhao Shihao Zhou Yue Wang Xiaoyu Yang Youhui Meng Yanxin Zhang Jian Gao national glycoengineering research center Shandong Key Laboratory of Carbohydrate Chemistry and GlycobiologyNMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based MedicineShandong UniversityQingdao 266237China Department of Pharmaceutical Engineering College of Chemical EngineeringNorthwest UniversityXi'an 710069China

A family of the 3,6-branched Fuziα-glucans including the pentasaccharide repeating unit as well as its di-and trimers were efficiently achieved via a one-pot and convergent glycosylation *** the protectedα-glucans up to 15-mer were assembled with high yields and excellentα-stereoselectivity,which was secured by the synergisticα-directing effects of the Tol SCl/Ag OTf promotion system and the stericβ-facial shielding of bulky saccharide residues linked at the 6-O-position of glucosyl ***,the 3,6-branched architecture of glycosyl donor was revealed to be more favorable for theα-selective glucosidation of primary hydroxyl group,especially in the case of large oligosaccharide *** structurally well-defined syntheticα-glucans would be useful for various biological studies.

关键词： α-D-Glucan One-pot synthesis Convergent glycosylation Stereoselective synthesis Thioglycoside

Capture-Release Strategy Facilitates Rapid Enzymatic Assembly of Oligosaccharides

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Chinese Journal of chemistry 2022年第3期40卷 343-350页

作者： Wenyuan Fang Kan Zhong Jiansong Cheng Xian-Wei Liu Chang-Cheng Liu Zhongfu Wang Hongzhi Cao national glycoengineering research center NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-Based Medicineand Shandong Key Laboratory of Carbohydrate Chemistry and GlycobiologyShandong UniversityQingdaoShandong 266237China key laboratory of Marine Drugs of Ministry of Education Shandong Key Laboratory of Glycoscience and GlycotechnoiogySchool of Medicine and PharmacyOcean University of ChinaQingdaoShandong 266003China College of Pharmacy Nonkoi UniversityTianjin 300071China glycobiology and Glycotechnology research center College of Food Science and TechnologyNorthwest UniversityXi'anShaanxi 710069China laboratory for Marine Drugs and Bioproducts Pilot Notional Laboratory for Marine Science and Technology(Qingdao)QingdaoShandong 266237China

A convenient and highly efficient strategy was developed for the simplification of enzymatic synthesis and purification of *** acceptors terminated with a thiol tag were extended by enzymatic modular assembly(EMA)in the aqueous phase,and the desired products were captured during solid-phase workup(SPW)using commercially available thiopropyl Sepharose 6B resin through a reversible disulfide ***,the products were released from solid-phase resin in the presence of dithio-threitol(DTT)as reducing agent and the resin could be recovered and *** strategy overcomes the uncertain influence of polymer-or ionic-supports commonly used in enzymatic glycosylation,and showed perfect compatibility with all 10 enzyme modules for the rapid assembly of a series of complex oligosaccharides.

关键词： Glycosylation Oligosaccharide synthesis Thiol tag Capture-release Biocatalysis

Enzyme-like C-H Oxidation of Glucosides Promoted by Visible Light

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CCS chemistry 2022年第11期4卷 3599-3608页

作者： Mingzhong Wu Qian Jiang Qiong Tian Tianyun Guo Feng Cai Shouchu Tang Jian Liu Xiaolei Wang State key laboratory of Applied Organic chemistry Department of Chemistry and School of PharmacyLanzhou UniversityLanzhou 730000 State key laboratory of Veterinary Etiological Biology OIE/National Foot and Mouth Disease Reference LaboratoryLanzhou UniversityLanzhou 730000 The national glycoengineering research center Shandong Provincial Key Laboratory of Carbohydrate Chemistry and GlycobiologyShandong UniversityQingdao 266237

To match nature’s prowess at using enzymes to make desired motifs in a regioselective fashion,we explore the use of visible light for the selective oxidation of the hydroxyl group to afford the corresponding *** highly admirable approach offers several advantages over the enzymatic approach in terms of yields and the scope of ***,we report the development of a simple visiblelight-promoted selective oxidation of unprotected glucosides that allows for inexpensive access to valuable keto-saccharide building *** method is employed on a variety of different natural and artificial glucosides,is operationally simple and scalable,and can be used to access keto-saccharides rapidly and inexpensively.

关键词： keto-saccharide selective oxidation unprotected glucoside visible-light