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Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin‐Binding Proteins
Author(s) -
Beck Joséphine,
Gharbi Sonia,
HertegFernea Adriana,
Vercheval Lionel,
Bebrone Carine,
Lassaux Patricia,
Zervosen Astrid,
MarchandBrynaert Jacqueline
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800812
Subject(s) - chemistry , phosphonate , ethyl bromoacetate , hydrolysis , trimethylsilyl , alkylation , bromide , carboxypeptidase a , penicillin , organic chemistry , phenacyl bromide , stereochemistry , enzyme , biochemistry , carboxypeptidase , antibiotics , catalysis
Aminophosphonic acids and aminobis(phosphonic acids) have been prepared by the alkylation of Schiff bases with methyl bromoacetate or ethyl acrylate. Other pathways, like the modified Pudovik reaction and Kabachnik–Fields reaction, have been considered for the synthesis of the α‐phosphonic bioisoster of aminocitrate. Partial or complete deprotection of the phosphonate ester have been realised by either acidic hydrolysis or by treatment with trimethylsilyl bromide. Evaluation against penicillin‐binding proteins has shown that our compounds are modest inhibitors of class A β‐lactamases, but have an interesting activity against R39 ( D , D ‐peptidase/carboxypeptidase). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)