Structure of a Derivative of Streptovaricin C Triacetate. Crystal and Molecular Structure of the Atropisomer of the Cyclic p-Bromobenzeneboronate Ester of Streptovaricin C Triacetate: Methylene Dichloride 1 : 1 Solvate

Andrew H.J. Wang, Iain C. Paul

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17 Citations (Scopus)

Abstract

The crystal and molecular structure of a p-bromobenzeneboronate ester of streptovaricin C triacetate has been determined by single-crystal x-ray methods. The derivative studied was of the atropisomer of the naturally occurring form of streptovaricin C triacetate and it crystallized as a 1:1 methylene dichloride solvate. The crystals are orthorhombic, a = 22.487 (8), b = 12.678 (5), and c = 19.723 (6) Å, with four molecules of C52H59BBrNO17-CH2Cl2 in the space group P212121. The structure has been refined to an R factor of 0.106 on 2148 nonzero reflections. A strong indication of the absolute configuration was obtained from the x-ray study. The relative configuration, absolute configuration, and conformation of the ansa ring in this derivative of streptovaricin are compared with those found in other derivatives of ansamycins that have been studied by x-rays. Some structural features that may have a bearing on the biological activity of these macrocyclic antibiotics are also described and discussed.

Original languageEnglish
Pages (from-to)4612-4619
Number of pages8
JournalJournal of the American Chemical Society
Volume98
Issue number15
DOIs
Publication statusPublished - Jul 1 1976
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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