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.
|Pages (de - à)||1071-1076|
|Nombre de pages||6|
|Etat de la publication||Publié - 2007|