Title

1H-NMR and 13C-NMR Spectral Assignments of Spiramycins I and III

Document Type

Article

Publication Date

3-1994

Publication Source

Pharmaceutical Research

Abstract

The spiramycins (1a-1c) are 16-membered macrolide antibiotics produced by the bacteria Streptomyces ambofaciens (1) (Scheme I). This series of compounds shows gram-positive antibacterial activity as well as antimicrobial activity against both Toxoplasma gondii and Cryptosporidium, two protozoans which can result in potentially fatal opportunistic infections associated with AIDS (2,3). Our interest in the spiramycins has been the production of spiramycin derivatives through chemical and biochemical modifications of the basic spiramycin chemical structure. To prove unambiguously the structure of any derivatives, a complete structural understanding of the spiramycins themselves was necessary. After a thorough search of the literature, we found various NMR structural characterizations of these compounds. Unfortunately, many of the structural aspects of the spiramycins are reported incorrectly or not at all. We have made the complete NMR spectral assignments of spiramycins I and III based on our interpretation of the NMR techniques of DEPTGL, HETCOR, HMBC, and COSY.

Inclusive pages

458–465

ISBN/ISSN

0724-8741

Comments

Permission documentation is on file.

Publisher

Springer

Volume

11

Issue

3

Peer Reviewed

yes