A simple and accessible synthetic lectin for glucose recognition and sensing.
Binding carbohydrates from water is a difficult task, even for the natural carbohydrate-binding proteins known as lectins. The design of synthetic lectin mimics is correspondingly challenging, especially if good selectivities are required. In previous work we showed that success is possible, but only for complex polycyclic architectures that require lengthy and low-yielding syntheses; for example, one glucose-selective system was made in 21 steps and only 0.1% overall yield. Here we report the discovery of a simple monocyclic host that matches the earlier designs, but is far more accessible as it is prepared in just five steps and 23% overall yield. The new synthetic lectin binds glucose with excellent selectivity versus other common monosaccharides (for example, ~50:1 versus galactose) and sufficient affinity for glucose sensing at the concentrations found in blood. It also features a built-in signalling system in the form of strong and guest-dependent fluorescence emission. The effectiveness and simplicity of this molecule suggests the potential for development into a new methodology for practical glucose monitoring.
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Chenfeng
C
Ke
Harry
H
Destecroix
Matthew P
MP
Crump
Anthony P
AP
Davis
D015374:Biosensing Techniques / Q000379:methods*; D005456:Fluorescent Dyes / Q000737:chemistry; D005947:Glucose / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D037102:Lectins / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D011485:Protein Binding; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D037102:Lectins; D005947:Glucose