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Synthetic Access to Hydrophilic Tetramate Derivatives of Cysteine
Author(s) -
Ruirui Zhang,
Xiang Li,
Miroslav Genov,
Alexander Pretsch,
Dagmar Pretsch,
Mark G. Moloney
Publication year - 2020
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01636
Subject(s) - chemistry , combinatorial chemistry , cysteine , bicyclic molecule , chelation , chemical synthesis , antibacterial activity , organic chemistry , stereochemistry , bacteria , in vitro , biochemistry , biology , genetics , enzyme
The synthesis, structural, and antibacterial evaluation of bicyclic tetramate derivatives of cysteine rendered hydrophilic with pendant heterocyclic substituents is reported; effective synthetic protocols and antibacterial activity for a small library of polar derivatives were found, and direct evidence for strong metal chelation in these systems was obtained. A computational study has developed a detailed understanding of the controlling factors of the key Dieckmann cyclization step.

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