Abstract
Despite the large number of articles and patents dealing with
penicillin and other b-lactam antibiotics, there have been no reports
about the self-assembly of such substances as monolayers
on gold surfaces. The main reason stems from the high reactivity
of the b-lactam ring, which hinders the development of molecules
possessing this entity together with a metal-anchoring function.
Herein, we present the synthesis of a novel molecule, 6-
[(R,S)-5-(1,2-dithiolan-3-yl)pentanoyl-amino]-penicillanic acid,which combines the b-lactam ring and a metal-anchoring group.
Using spectroscopic tools, we demonstrate the chemisorption of
this compound on gold as self-assembled monolayers without
any alteration of the penicillin pharmacophore and document its
reactivity towards a penicillin-binding protein, BlaR-CTD. Our
work is a preliminary step towards the development of new biosensors
and well-ordered protein arrays, both based on the high
affinity of penicillin for penicillin-binding proteins.
Original language | English |
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Pages (from-to) | 1071-1076 |
Number of pages | 6 |
Journal | ChemPhysChem |
Volume | 8 |
Publication status | Published - 2007 |
Keywords
- antibiotics · chemisorption · immobilization · monolayers · synthetic methods