Ph3PO-Modulated Kdo Glycosidation for Stereoselective Synthesis of β-Kdo-Containing Disaccharides DOI
Miao He,

Ruihao Yu,

Jibin Zheng

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 30, 2024

A Ph3PO-modulated β-selective Kdo glycosidation approach is developed for the stereoselective synthesis of β-Kdo glycosides. With readily available per-O-acetylated ynenoate as donor, glycosylation with a series alcohols in presence Ph3PAuOTf and Ph3PO toluene at low temperatures afforded desired glycosides good to excellent β-selectivities. Furthermore, was effectively applied β-(2→4)- β-(2→8)-linked Kdo-Kdo disaccharides further biological studies.

Язык: Английский

Pseudomonas aeruginosa Vaccine Development: Lessons, Challenges, and Future Innovations DOI Open Access

Rebeca Santamarina-Fernández,

Víctor Fuentes-Valverde,

Alis Silva-Rodríguez

и другие.

International Journal of Molecular Sciences, Год журнала: 2025, Номер 26(5), С. 2012 - 2012

Опубликована: Фев. 25, 2025

Pseudomonas aeruginosa is an opportunistic pathogen with a multidrug-resistant profile that has become critical threat to global public health. It one of the main causes severe nosocomial infections, including ventilator-associated pneumonia, chronic infections in patients cystic fibrosis, and bloodstream immunosuppressed individuals. Development vaccines against P. major challenge owing high capacity this bacterium form biofilms, its wide arsenal virulence factors (including secretion systems, lipopolysaccharides, outer membrane proteins), ability evade host immune system. This review provides comprehensive historical overview vaccine development efforts targeting pathogen, ranging from early attempts 1970s recent advancements, based on novel proteins emerging technologies such as nanoparticles synthetic conjugates. Despite numerous promising preclinical developments, very few candidates have progressed clinical trials, none achieved final approval. panorama highlights significant scientific undertaken inherent complexity successfully developing effective aeruginosa.

Язык: Английский

Процитировано

0

Residue-Specific Protein-Glycan Conjugation Strategies for the Development of Pharmaceutically Promising Glycoconjugate Vaccines: A Recent Update DOI
Rajib Sarkar, A. Bandyopadhyay, Goutam Brahmachari

и другие.

Carbohydrate Research, Год журнала: 2025, Номер unknown, С. 109476 - 109476

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0

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

Photolabile ortho‐Nitro‐Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol DOI
Jibin Zheng, Hongyu Chen,

Jintao Shang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 16, 2024

Comprehensive Summary Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize photolabile ortho ‐nitro‐benzyl carbonate ( o NBC) as a permanent hydroxyl group for stereocontrolled The Ph 3 PO‐modulated glycosylation strongly disarmed per‐ O ‐ NBC‐protected glycosyl ynenoates preferred afford glycosides excellent α‐selectivities via β‐phosphonium transition state. Based on NBC‐mediated galactosylation, glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds two esters was achieved in straightforward manner.

Язык: Английский

Процитировано

2

Ph3PO-Modulated Kdo Glycosidation for Stereoselective Synthesis of β-Kdo-Containing Disaccharides DOI
Miao He,

Ruihao Yu,

Jibin Zheng

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 30, 2024

A Ph3PO-modulated β-selective Kdo glycosidation approach is developed for the stereoselective synthesis of β-Kdo glycosides. With readily available per-O-acetylated ynenoate as donor, glycosylation with a series alcohols in presence Ph3PAuOTf and Ph3PO toluene at low temperatures afforded desired glycosides good to excellent β-selectivities. Furthermore, was effectively applied β-(2→4)- β-(2→8)-linked Kdo-Kdo disaccharides further biological studies.

Язык: Английский

Процитировано

0