New H-bonding patterns in biphenyl-based synthetic lectins; pyrrolediamine bridges enhance glucose-selectivity.
Synthetic lectins are molecules designed for the challenging task of biomimetic carbohydrate recognition in water. Previous work has explored a family of such systems based on bi/terphenyl units as hydrophobic surfaces and isophthalamide spacers to provide polar binding groups. Here we report a related receptor which employs a new spacer, 2,5-bis-(aminomethyl)-pyrrole, with an alternative (A-D-A) set of H-bonding valencies. The modified spacer leads to significant changes in binding selectivity, including a preference for glucose over all other tested substrates.
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS1 1TS, UK.
Gururaj
G
Joshi
Anthony P
AP
Davis
D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D001713:Biphenyl Compounds / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry*; D005947:Glucose / Q000378:metabolism*; D006860:Hydrogen Bonding; D037102:Lectins / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D011758:Pyrroles / Q000737:chemistry*; D013379:Substrate Specificity
D001713:Biphenyl Compounds; D003959:Diamines; D005947:Glucose; D037102:Lectins; D011758:Pyrroles; C010574:biphenyl