Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water.
Angew Chem Int Ed Engl
; 55(32): 9311-5, 2016 08 01.
Article
em En
| MEDLINE
| ID: mdl-27312071
ABSTRACT
Biomimetic carbohydrate receptors ("synthetic lectins") have potential as agents for biological research and medicine. However, although effective strategies are available for "all-equatorial" carbohydrates (glucose, etc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report a new approach based on a pyrene platform with polar arches extending from aryl substituents. The receptors are compatible with axially substituted carbohydrates, and also feature two identical binding sites, thus mimicking the multivalency observed for natural lectins. A variant with negative charges forms 12 host/guest complexes with aminosugars, with K1 >3000 m(-1) for axially substituted mannosamine, whereas a positively charged version binds the important α-sialyl unit with K1 ≈1300 m(-1) .
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirenos
/
Água
/
Corantes Fluorescentes
/
Lectinas
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2016
Tipo de documento:
Article
País de afiliação:
Reino Unido