Chemical Synthesis of Acetobacter pasteurianus Lipid A with a Unique Tetrasaccharide Backbone and Evaluation of Its Immunological Functions.
Angew Chem Int Ed Engl
; 63(24): e202402922, 2024 06 10.
Article
em En
| MEDLINE
| ID: mdl-38581637
ABSTRACT
Lipopolysaccharide (LPS), a cell surface component of Gram-negative bacteria, activates innate immunity. Its active principle is the terminal glycolipid lipidâ
A. Acetobacter pasteurianus is a Gram-negative bacterium used in the fermentation of traditional Japanese black rice vinegar (kurozu). In this study, we focused on A.â
pasteurianus lipidâ
A, which is a potential immunostimulatory component of kurozu. The active principle structure of A.â
pasteurianus lipidâ
A has not yet been identified. Herein, we first systematically synthesized three types of A.â
pasteurianus lipidâ
As containing a common and unique tetrasaccharide backbone. We developed an efficient method for constructing the 2-trehalosamine skeleton utilizing borinic acid-catalyzed glycosylation to afford 1,1'-α,α-glycoside in high yield and stereoselectivity. A common tetrasaccharide intermediate with an orthogonal protecting group pattern was constructed via [2+2] glycosylation. After introducing various fatty acids, all protecting groups were removed to achieve the first chemical synthesis of three distinct types of A.â
pasteurianus lipidâ
As. After evaluating their immunological function using both human and murine cell lines, we identified the active principles of A.â
pasteurianus LPS. We also found the unique anomeric structure of A.â
pasteurianus lipidâ
A contributes to its high chemical stability.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Acetobacter
/
Lipídeo A
Limite:
Animals
/
Humans
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
Japão