82198-76-3Relevant articles and documents
Attempted introduction of a fourth amide NH into the carboxylate-binding pocket of glycopeptide antibiotics
Goerlitzer, Jochen,Gale, Thomas F.,Williams, Dudley H.
, p. 3253 - 3257 (1999)
We report the synthesis of a novel derivative of the glycopeptide antibiotic vancomycin, modified at the N-terminus. This incorporates a fourth amide NH into the antibiotic, at the position which was formerly the N-terminus of the antibiotic-binding pocke
Impurity Identification and Scale-Up of a Novel Glycopeptide Antibiotic
Guan, Dongliang,Huang, Wei,Jiao, Shang,Li, Jian,Liu, Bo,Shi, Weiwei,Tang, Feng,Xu, Lili
, p. 2390 - 2402 (2021/11/01)
A variety of novel glycopeptide antibiotics have been developed to combat the drug-resistant bacterial strains. Previously, we reported a series of vancomycin derivatives that are modified with lipid tails and extra sugars. SM-V-61, as one of the vancomycin analogues with a trifluoromethyl-biphenyl fragment and galactose, showed enhanced antibacterial activity, improved PK/PD, better water solubility, and safety. However, the deficient synthetic procedure, lower yield, and complicated impurities hindered the further development of the drug candidate SM-V-61. Herein, we reported a further study on SM-V-61 impurity analysis and process optimization. We first synthesized and identified a variety of impurities and established the analytical method for quality analysis and control of SM-V-61. Based on the defined analytical method, we optimized the synthetic procedure for SM-V-61 and operated the synthesis on 30-40 and 500-600 g scales in the laboratory and manufacturing workshop, respectively.
Vancomycin-Dependent Response in Live Drug-Resistant Bacteria by Metabolic Labeling
Pidgeon, Sean E.,Pires, Marcos M.
supporting information, p. 8839 - 8843 (2017/07/17)
The surge in drug-resistant bacterial infections threatens to overburden healthcare systems worldwide. Bacterial cell walls are essential to bacteria, thus making them unique targets for the development of antibiotics. We describe a cellular reporter to directly monitor the phenotypic switch in drug-resistant bacteria with temporal resolution. Vancomycin-resistant enterococci (VRE) escape the bactericidal action of vancomycin by chemically modifying their cell-wall precursors. A synthetic cell-wall analogue was developed to hijack the biosynthetic rewiring of drug-resistant cells in response to antibiotics. Our study provides the first in vivo VanX reporter agent that responds to cell-wall alteration in drug-resistant bacteria. Cellular reporters that reveal mechanisms related to antibiotic resistance can potentially have a significant impact on the fundamental understanding of cellular adaption to antibiotics.
Structure-activity relationship studies of a series of antiviral and antibacterial aglycon derivatives of the glycopeptide antibiotics vancomycin, eremomycin, and dechloroeremomycin
Printsevskaya, Svetlana S.,Solovieva, Svetlana E.,Olsufyeva, Eugenia N.,Mirchink, Elena P.,Isakova, Elena B.,De Clercq, Erik,Balzarini, Jan,Preobrazhenskaya, Maria N.
, p. 3885 - 3890 (2007/10/03)
N-Adamantyl-1)methyl, N-(adamantyl-2), and N-(ω-aminodecyl) amides of vancomycin, eremomycin, and dechloroeremomycin aglycons and their des-(N-Me-D-Leu) derivatives were synthesized and their antibacterial and anti-HIV activities were investigated. Carbox
