Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water.
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 1:2 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) .
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Tom S
0000-0001-6488-1028
TS
Carter
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Tiddo J
TJ
Mooibroek
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Patrick F N
PF
Stewart
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Matthew P
0000-0002-7868-5818
MP
Crump
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
M Carmen
MC
Galan
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK. Anthony.Davis@bristol.ac.uk.
Anthony P
0000-0001-5213-624X
AP
Davis
D005456:Fluorescent Dyes / Q000032:analysis*; D037102:Lectins / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011721:Pyrenes / Q000032:analysis*; D014867:Water / Q000737:chemistry*
D005456:Fluorescent Dyes; D037102:Lectins; D011721:Pyrenes; D014867:Water; C030984:pyrene
carbohydrates; dendrimers; molecular recognition; receptors; supramolecular chemistry