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.

Journal of the American Chemical Society
Akinori OkanoDale L Boger

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.

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Citations

Aug 15, 2014·The Journal of Antibiotics·Mark S ButlerMatthew A Cooper
Jan 7, 2016·Organic Letters·Jianpeng WeiXuefeng Jiang
Aug 27, 2013·Expert Opinion on Therapeutic Patents·Eugenia N Olsufyeva, Maria N Preobrazhenskaya
Apr 25, 2017·Chemical Reviews·Akinori OkanoDale L Boger
Mar 27, 2015·Organic & Biomolecular Chemistry·Yanxin J WangE James Petersson
Jun 1, 2017·Proceedings of the National Academy of Sciences of the United States of America·Akinori OkanoDale L Boger
Nov 2, 2019·The Journal of Biological Chemistry·Edward MarschallJulien Tailhades
Jun 30, 2016·Biopolymers·Marta De ZottiClaudio Toniolo
Dec 17, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Sida WangFrank T Edelmann
Nov 19, 2020·Organic Letters·Sungjoon HuhAndrei K Yudin
Jan 23, 2019·Journal of the American Chemical Society·Binbin LiuXihe Bi
May 23, 2013·Journal of the American Chemical Society·Tejas P Pathak, Scott J Miller
Jul 29, 2020·ACS Central Science·Melissa A HardyRichmond Sarpong
Jan 25, 2018·ACS Infectious Diseases·Mark A T BlaskovichMatthew A Cooper
Jan 31, 2019·ACS Chemical Biology·Nilkamal MahantaDouglas A Mitchell
Nov 4, 2020·Accounts of Chemical Research·Zhi-Chen Wu, Dale L Boger

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