Solvent affects the conformation of virginiamycin M1				(pristinamycin IIA, streptogramin A)

Jason Dang; Mikael Bergdahl; Frances Separovic; Robert T. C. Brownlee; Robert P. Metzger

doi:10.1039/B407724E

Solvent affects the conformation of virginiamycin M₁ (pristinamycin IIA, streptogramin A)†

Jason Dang,^a Mikael Bergdahl,^b Frances Separovic,^c Robert T. C. Brownlee^d and Robert P. Metzger*^e

* Corresponding authors

^a School of Chemistry, LaTrobe University, VIC, Australia
E-mail: j.dang@latrobe.edu.au
Fax: 61 3 9479 1399
Tel: 61 3 9479 2582

^b Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA, USA
E-mail: bergdahl@sciences.sdsu.edu
Fax: 01 619 594 4634
Tel: 1-619 594 5865

^c School of Chemistry, The University of Melbourne, VIC, Australia
E-mail: fs@unimelb.edu.au
Fax: 61 3 9347 5180
Tel: 61 3 8344 6464

^d School of Chemistry, LaTrobe University, VIC, Australia
E-mail: r.brownlee@latrobe.edu.au
Fax: 61 3 9479 1399
Tel: 61 3 9479 2547

^e Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA, USA
E-mail: rmetzger@sciences.sdsu.edu
Fax: 1 619 594 4634
Tel: 1 619 594 6801

Abstract

The streptogramins are antibiotics which act by binding two different components at separate nearby sites on the bacterial 50S ribosome, inhibiting protein synthesis. The first component, a macrolactone, is common to many of the streptogramin antibiotics and, thus, is referred to by many names including virginiamycin M₁ (VM1), pristinamycin IIA, ostreogrycin A and streptogramin A. X-Ray crystallographic studies of VM1 bound to ribosomes and to a deactivating enzyme show a different conformation to that of VM1 in chloroform solution. We now report the results of high resolution 2D NMR experiments that show that the conformation of VM1 in dimethyl sulfoxide and methanol differs from both that in chloroform solution and in the bound form. The 3D structure and the ¹H NMR and ¹³C NMR chemical shifts of VM1 in dimethyl sulfoxide and methanol are described.

Article information

https://doi.org/10.1039/B407724E

Article type

Paper

Submitted

25 May 2004

Accepted

16 Aug 2004

First published

16 Sep 2004

Download Citation

Org. Biomol. Chem., 2004,2, 2919-2924

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Solvent affects the conformation of virginiamycin M₁ (pristinamycin IIA, streptogramin A)

J. Dang, M. Bergdahl, F. Separovic, R. T. C. Brownlee and R. P. Metzger, Org. Biomol. Chem., 2004, 2, 2919 DOI: 10.1039/B407724E

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Organic & Biomolecular Chemistry