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J Am Chem Soc. 2012 May 30;134(21):8790-3. doi: 10.1021/ja302808p. Epub 2012 May 17.

Silver(I)-promoted conversion of thioamides to amidines: divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands.

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1
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Abstract

Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed. This reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction with model ligands of peptidoglycan precursors and explore their resulting impact on antimicrobial properties.

PMID:
22568755
PMCID:
PMC3365631
DOI:
10.1021/ja302808p
[Indexed for MEDLINE]
Free PMC Article

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