Chemistry:Pristinamycin IIA
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| Other names | Mikamycin A; Virginiamycin M1 |
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| Formula | C28H35N3O7 |
| Molar mass | 525.602 g·mol−1 |
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Pristinamycin IIA is a macrolide antibiotic. It is a member of the streptogramin A group of antibiotics and one component of pristinamycin (the other being pristinamycin IA).[1] Pristinamycin IIA was first isolated from the Streptomyces virginiae, but has been isolated from other microorganisms and thus has been given a variety of other names such as Virginiamycin M1, Mikamycin A, and Streptogramin A.[2] Pristinamycin IIA structure was determined by chemical and instrumental techniques, including X-ray crystallography.[2][3] Pristinamycin IIA is of interest from a biosynthetic viewpoint because it contains the unusual dehydroproline and oxazole ring systems.[2] The only experimental evidence bearing on the formation of the oxazole ring is found in work on the biosynthesis of the alkaloid annuloline.[2][4]
Biosynthesis
Pristinamycin IIA biosynthesis is presumed to proceed through the acetate pathway and was determined through the feeding of 3H and 13C precursors to Streptomyces virginiae strain PDT-30.[2] When fed [2-13C]-acetate the 13C NMR Spectra showed signals corresponding to carbons 5, 9, 10a, 11, 13, and 15 seen in the biosynthesis scheme.[2] In addition, methionine was found to donate its methyl group specifically to carbon-3 (seen in the biosynthesis scheme) by studies with L-[methyl-13C] methionine.[2] With this data and the known incorporation of proline, methionine, serine, and glycine into the antibiotic along with the assumption that carbon atoms 1, la, lb, and 2 are derived from valine or isobutyric acid, allows for a tentative pathway for the biosynthesis of Pristinamycin IIA to be deduced.[2] File:Virginiamycin M1 Biosynthesis 3.tif
See also
References
- ↑ "Comparative in vitro activities of pristinamycin, its components, and other antimicrobial agents against anaerobic bacteria". Antimicrobial Agents and Chemotherapy 32 (7): 1094–1096. July 1988. doi:10.1128/AAC.32.7.1094. PMID 3142342.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 "Biosynthesis of antibiotics of the virginiamycin family. 1. Biosynthesis of virginiamycin M1: determination of the labeling pattern by the use of stable isotope techniques". Journal of the American Chemical Society 102 (18): 5964–5966. August 1980. doi:10.1021/ja00538a070. https://pubs.acs.org/doi/pdf/10.1021/ja00538a070. Retrieved 29 May 2022.
- ↑ "Antibiotics of the ostreogrycin complex. II. Structure of ostreogrycin A". Journal of the Chemical Society, Perkin Transactions 1 19: 1653–1669. 1966. doi:10.1039/j39660001653. PMID 5950461.
- ↑ "The biosynthesis of annuloline, a unique oxazole alkaloid". Journal of the Chemical Society C: Organic 1: 331–334. 1971. doi:10.1039/J39710000331.
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