Synthesis of a pentasaccharide and neoglycoconjugates related to fungal α-(1â3)-glucan and their use in the generation of antibodies to trace Aspergillus fumigatus cell wall.
Chemistry
; 21(3): 1029-35, 2015 Jan 12.
Article
em En
| MEDLINE
| ID: mdl-25376936
ABSTRACT
3-Aminopropyl α-(1â3)-pentaglucoside, a fragment of α-(1â3)-glucan of the cell wall of Aspergillus fumigatus, has been synthesized in a blockwise approach. The application of mono- and disaccharide N-phenyltrifluoroacetimidates bearing a stereodirecting 6-O-benzoyl group was essential for stereoselective α-glucosylations. In the products, p-methoxyphenyl and levulinoyl groups served as orthogonal protecting groups for the anomeric position and 3-OH group, respectively. Their removal from shared blocks led to donors and acceptors that were used for the synthesis of pentasaccharides. Coupling of free α-(1â3)-pentaglucoside with biotin and bovine serum albumin (BSA) gave glycoconjugate tools for mycological studies. Immunization of mice with the BSA conjugate induced the generation of antibodies that recognize α-(1â3)-glucan on A. fumigatus cell wall and distinguish its morphotypes. This discovery represents a first step to the development of a diagnostic test system and a vaccine to detect and fight this life-threatening pathogen.
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MEDLINE
Assunto principal:
Oligossacarídeos
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Aspergillus fumigatus
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Glicoconjugados
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Glucanos
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Anticorpos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article