Ribostamycinribostamycin sulfate, ribostamycin
Ribostamycin is an aminoglycoside-aminocyclitol antibiotic isolated from a streptomycete, Streptomyces ribosidificus, originally identified in a soil sample from Tsu City of Mie Prefecture in Japan It is made up of 3 ring subunits: 2-deoxystreptamine DOS, neosamine C, and ribose Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization, Resistance against aminoglycoside antibiotics, such as ribostamycin, is a growing concern The resistant bacteria contain enzymes that modify the structure through phosphorylation, adenylation, and acetylation and prevent the antibiotic from being able to interact with the bacterial ribosomal RNAs
The biosynthesis of ribostamycin begins with the sugar, D-glucose, which is phosphorylated at the 6 position to form glucose-6-phosphate Enzyme rbmA contains a genetic sequence that corresponds to NAD+ binding and catalyzes the formation of 2-deoxy-scyllo-inosose Enzyme rmbB then catalyzes the transamination of 2-deoxy-scyllo-inosose to 2-deoxy-scyllo-inosamine with L-glutamine and pyridoxal phosphate PLP Enzyme rbmC oxidizes the ring to 2-deoxy-3-amino-scyllo-inosose, which is then transaminated by enzyme rmbB to DOS DOS is then glycosylated by the glycosyltransferase rmbD with uridine diphosphate N-acetylglucosamine UDP-Glc-NAc to form 2’-N-acetylparomamine The deacetylase, racJ, removes the acetyl group and forms paromamine Paromamine is oxidized by enzyme rbmG and then enzyme rmbH transaminates to produce neamine Neamine is then ribosylated to form ribostamycin,
- ^ Shomura, T; Ezaki, N; Tsuruoka, T; Niwa, T; Akita, E; Niida, T; Studies on Antibiotic SF-733, a New Antibiotic I Taxonomy, Isolation and Characterization The Journal of Antibiotics 1970, 23 3, 155-161
- ^ a b Subba, B; Kharel, MK; Lee, HC; Liou, K; Kim, BG; Sohng, JK; The Ribostamycin Biosynthetic Gene Cluster in Streptomyces ribosidificus: Comparison With Butirosin Biosynthesis Molecules and Cells 2005, 20 1, 90-96
- ^ a b Kurumbang NP; Liou, K; Sohng, JK; Biosynthesis of Ribostamycin Derivatives by Reconstitution and Heterologous Expression of Required Gene Sets Applied Biochemistry and Biotechnology 2011, 163, 373-382
- ^ World Health Organization Critically Important Antimicrobials for Human Medicine 3rd revision 2011
- ^ Kudo, F; Eguchi, T; Biosynthetic Genes for Aminoglycoside Antibiotics The Journal of Antibiotics 2009, 62, 471-481
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ribostamycin, ribostamycin sulfate
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