Promoter‐Controlled Synthesis and Conformational Analysis of Cyclic Mannosides up to a 32‐mer DOI
Xiaona Li, Cristina Di Carluccio, Miao He

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(43)

Опубликована: Июль 12, 2023

Abstract Cyclodextrins are widely used as carriers of small molecules for drug delivery owing to their remarkable host properties and excellent biocompatibility. However, cyclic oligosaccharides with different sizes shapes limited. Cycloglycosylation ultra‐large bifunctional saccharide precursors is challenging due the constrained conformational spaces. Herein we report a promoter‐controlled cycloglycosylation approach synthesis α‐(1→6)‐linked mannosides up 32‐mer. thioglycosides ( Z )‐ynenoates was found be highly dependent on promoters. In particular, sufficient amount gold(I) complex played key role in proper preorganization transition state, providing 32‐mer polymannoside, which represents largest synthetic polysaccharide date. NMR experiments computational study revealed that 2‐mer, 4‐mer, 8‐mer, 16‐mer, adopted states shapes.

Язык: Английский

Recent advances in therapeutic targets identification and development of treatment strategies towards Pseudomonas aeruginosa infections DOI Creative Commons
Daniel Ruben Akiola Sanya, Djamila Onésime, Grazia Vizzarro

и другие.

BMC Microbiology, Год журнала: 2023, Номер 23(1)

Опубликована: Март 30, 2023

Abstract The opportunistic human pathogen Pseudomonas aeruginosa is the causal agent of a wide variety infections. This non-fermentative Gram-negative bacillus can colonize zones where skin barrier weakened, such as wounds or burns. It also causes infections urinary tract, respiratory system bloodstream. P. are common in hospitalized patients for which multidrug-resistant, respectively extensively drug-resistant isolates be strong contributor to high rate in-hospital mortality. Moreover, chronic cystic fibrosis especially concerning, since very tedious treat. exploits diverse cell-associated and secreted virulence factors, play essential roles its pathogenesis. Those factors encompass carbohydrate-binding proteins, quorum sensing that monitor production extracellular products, genes conferring extensive drug resistance, secretion deliver effectors kill competitors subvert host functions. In this article, we highlight recent advances understanding pathogenicity well efforts identification new targets development therapeutic strategies against These provide innovative promising circumvent infection caused by important pathogen.

Язык: Английский

Процитировано

45

Glycoconjugate vaccines against antimicrobial resistant pathogens DOI Creative Commons
Charlotte Sorieul, Marta Dolce, Maria Rosaria Romano

и другие.

Expert Review of Vaccines, Год журнала: 2023, Номер 22(1), С. 1055 - 1078

Опубликована: Окт. 30, 2023

Introduction Antimicrobial resistance (AMR) is responsible for the death of millions worldwide and stands as a major threat to our healthcare systems, which are heavily reliant on antibiotics fight bacterial infections. The development vaccines against main pathogens involved urgently required prevention remains essential rise AMR.

Язык: Английский

Процитировано

18

Synthesis of Nucleosides and Deoxynucleosides via Gold(I)-Catalyzed N-Glycosylation of Glycosyl (Z)-Ynenoates DOI
Rongkun Liu, Yan Chen, Jibin Zheng

и другие.

Organic Letters, Год журнала: 2022, Номер 24(51), С. 9479 - 9484

Опубликована: Дек. 16, 2022

Nucleoside analogues are widely used as anticancer and antiviral drugs. Here, we develop a highly efficient gold(I)-catalyzed N-glycosylation approach for versatile synthesis of various types nucleosides deoxynucleosides with glycosyl (Z)-ynenoates donors. The wide scope the was demonstrated by 31 pyrimidine 8 purine nucleosides. Remarkably, pyranosyl purines found to be very effective regioselective N9 Based on catalytic approach, convenient two 5'-deoxynucleosides drugs (capecitabine galocitabine), four 2'-deoxynucleoside (floxuridine, trifluridine, decitabine cladribine), 3',5'-dideoxynucleoside analogues, 2',5'-dideoxynucleoside achieved in collective manner.

Язык: Английский

Процитировано

25

Promoter‐Controlled Synthesis and Conformational Analysis of Cyclic Mannosides up to a 32‐mer DOI
Xiaona Li, Cristina Di Carluccio, Miao He

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(43)

Опубликована: Июль 12, 2023

Cyclodextrins are widely used as carriers of small molecules for drug delivery owing to their remarkable host properties and excellent biocompatibility. However, cyclic oligosaccharides with different sizes shapes limited. Cycloglycosylation ultra-large bifunctional saccharide precursors is challenging due the constrained conformational spaces. Herein we report a promoter-controlled cycloglycosylation approach synthesis α-(1→6)-linked mannosides up 32-mer. thioglycosides (Z)-ynenoates was found be highly dependent on promoters. In particular, sufficient amount gold(I) complex played key role in proper preorganization transition state, providing 32-mer polymannoside, which represents largest synthetic polysaccharide date. NMR experiments computational study revealed that 2-mer, 4-mer, 8-mer, 16-mer, adopted states shapes.

Язык: Английский

Процитировано

12

A Semisynthetic Oligomannuronic Acid-Based Glycoconjugate Vaccine against Pseudomonas aeruginosa DOI Creative Commons
Yiyue Zhang,

Xiaotong Wang,

Youling Liang

и другие.

ACS Central Science, Год журнала: 2024, Номер 10(8), С. 1515 - 1523

Опубликована: Июль 10, 2024

is one of the leading causes nosocomial infections and has become increasingly resistant to multiple antibiotics. However, development novel classes antibacterial agents against multidrug-resistant

Язык: Английский

Процитировано

5

Synthesis and application of bacterial exopolysaccharides DOI Creative Commons
Gijs Ruijgrok,

Dung‐Yeh Wu,

Herman S. Overkleeft

и другие.

Current Opinion in Chemical Biology, Год журнала: 2023, Номер 78, С. 102418 - 102418

Опубликована: Дек. 21, 2023

Exopolysaccharides are produced and excreted by bacteria in the generation of biofilms to provide a protective environment. These polysaccharides generally generated as heterogeneous polymers varying length, featuring diverse substitution patterns. To obtain well-defined fragments these polysaccharides, organic synthesis often is method choice, it allows for full control over chain length installation pre-determined pattern. This review presents several recent syntheses exopolysaccharide Pseudomonas aeruginosa Staphylococcus aureus illustrates how have been used study biosynthesis enzymes generate synthetic glycoconjugate vaccines.

Язык: Английский

Процитировано

11

Chemical Synthesis and Antigenic Evaluation of Oligosaccharides of Bordetella hinzii O-Antigen Containing Unique Amidated 2,3-Diacetamido-2,3-dideoxy-alduronic Acids DOI Creative Commons
Lin Zhang, Zhichao Zheng, Yumeng Zhang

и другие.

JACS Au, Год журнала: 2025, Номер 5(4), С. 1903 - 1913

Опубликована: Апрель 16, 2025

Bordetella hinzii is a zoonotic pathogen, which can cause brain abscess, pneumonia, bacteremia, and urinary tract infection. Vaccines are economical effective means for combating infectious diseases. Herein, we present the first total synthesis of highly functionalized mono- oligosaccharides B. O-antigen vaccine development. The rare 2,3-diacetamidopyranoses were generated from 3-O-acetyl-2-nitroglycals via an organocatalyzed one-pot relay glycosylation method. postglycosylation oxidation strategy was used to overcome poor reactivity 2,3-diacetamido-aldouronic acid building blocks in reactions. Direct amidation alduronic with NH3 late stage reduced protecting group operation increased synthetic efficiency. Di-tert-butylsilylidene-directed α-galactosylation method construct challenging 1,2-cis-glycosidic bond. Six obtained further conjugated human serum albumin antigenicity evaluation (the sera antibodies vaccinated mouse inactivated hinzii). terminal tetrasaccharide has been identified as potential glycol-epitope might be useful development against hinzii.

Язык: Английский

Процитировано

0

Total Synthesis of the Tetrasaccharide Repeating Unit of Pseudomonas aeruginosa Serotype 4 O‐Antigen DOI

Xiaopeng Zou,

Junxi Zhang,

Yilei Lu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

Comprehensive Summary Pseudomonas aeruginosa is an opportunistic pathogen responsible for cystic fibrosis, bloodstream infections and hospital‐acquired pneumonia. The O‐antigen of lipopolysaccharide on the cell surface P. has been identified as a promising target development carbohydrate‐based vaccines. In this study, we present first total synthesis tetrasaccharide repeating unit serotype 4 using linear [((1+1)+1)+1] glycosylation strategy. All rare amino sugars were synthesized from commercially available monosaccharides. formation 1,2‐ cis L‐fucosamine glycosidic bonds was achieved with high efficiency stereoselectivity by judicious choice C3/C4‐OH protecting groups L‐fucosamine. N ‐phenyl trifluoroacetimidate glycosyl donors have proven to be more efficient than selenoglycoside or thioglycoside during glycosylation, particularly when coupling low‐reactivity C3‐OH group O4‐Bz protected L‐FucN 3 acceptor. TBSOTf demonstrated higher efficacy catalyst compared TMSOTf promoting less reactive acceptors. synthetic O‐antigen, which incorporates pentyl amine linker at reducing end, prepared conjugation carrier proteins utilization in microarray studies aimed further immunological investigations.

Язык: Английский

Процитировано

0

Microwave-assisted synthesis of highly sulfated mannuronate glycans as potential inhibitors against SARS-CoV-2 DOI

Yirong Zhu,

Xiaotong Wang,

Siqian Lu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(19), С. 3986 - 3994

Опубликована: Янв. 1, 2024

Sulfated mannuronate glycans with up to 17 sulfation sites were synthesized using a microwave-assisted approach and evaluated as inhibitors against SARS-CoV-2.

Язык: Английский

Процитировано

2

Expeditious chemical synthesis of xylomannans disproves the proposed antifreeze activities DOI Creative Commons
Qian Zhu, Simone Nicolardi,

Yuanguang Wang

и другие.

National Science Review, Год журнала: 2024, Номер 11(10)

Опубликована: Авг. 23, 2024

ABSTRACT Cold-adapted species are able to generate cryoprotective proteins and glycoproteins prevent freezing damage. The [→4)-β-D-Manp-(1→4)-β-D-Xylp-(1→]n xylomannan from the Alaska beetle Upis ceramboides was disclosed by Walters co-workers in 2009 as first glycan-based antifreeze agent, which later reported be found diverse taxa. Here, we report rapid synthesis of four types xylomannans, including proposed up a 64-mer (Type I), regioisomeric [→3)-β-D-Manp-(1→4)-β-D-Xylp-(1→]n 16-mer II), diastereomeric [→4)-β-L-Manp-(1→4)-β-D-Xylp-(1→]n III) block-wise [→4)-β-D-Manp-(1→]m[→4)-β-D-Xylp-(1→]n 32-mer IV), employing strategic iterative exponential glycan growth (IEGG) process. nuclear magnetic resonance spectral data alleged natural accordance only those Type IV none these synthetic xylomannans has been capable inducing thermal hysteresis. These results disprove previous reports about occurrence xylomannans.

Язык: Английский

Процитировано

2