Formation, isolation and characterization of an AB-biaryl atropisomer of oritavancin

Autor:	Eric W. Kristensen, Eric J. Stoner, Gregory M. Brill, Alan Christesen, Casey Chun Zhou, Kent D. Stewart, Edmund D. Matayoshi, Steven J. Wittenberger, L. Steven Hollis, Ronald R. Rasmussen
Rok vydání:	2004
Předmět:	Atropisomer Preparative hplc Molecular model Chemistry Stereochemistry medicine.drug_class Organic Chemistry Oritavancin Nuclear magnetic resonance spectroscopy Glycopeptide antibiotic Biochemistry Glycopeptide Drug Discovery medicine Vancomycin medicine.drug
Zdroj:	Tetrahedron. 60:10611-10618
ISSN:	0040-4020
Popis:	Oritavancin is a semi-synthetic glycopeptide antibiotic which is structurally related to vancomycin. When oritavancin bisphosphate is dried in vacuo with heat, a new compound forms. This new compound is stable only in the solid state and reverts to oritavancin in solution. Highly enriched samples of this compound were obtained by preparative HPLC and the structure of this compound was elucidated by using one and two-dimensional ( 1 H and 13 C) NMR spectroscopy in conjunction with computer-assisted molecular modeling. It has been determined that oritavancin adopts a conformation similar to that of vancomycin in solution, while the new compound is the unnatural R -AB-biaryl atropisomer of oritavancin. This is the first observation and isolation of an AB-biaryl atropisomer in an intact member of the vancomycin family of glycopeptide antibiotics.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a2095a1b5434e682347c40cb775e4e17 https://doi.org/10.1016/j.tet.2004.09.019 Zobrazit plný text záznamu Full Text from ScienceDirect