 | |
| Clinical data | |
|---|---|
| Other names | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol |
| AHFS/Drugs.com | International Drug Names |
| ATC code | |
| Identifiers | |
| |
| CAS Number |
|
| PubChemCID | |
| ChemSpider |
|
| UNII | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.053.421 |
| Chemical and physical data | |
| Formula | C17H34N4O10 |
| Molar mass | 454.477 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
 N Y (what is this?) (verify) | |
Ribostamycin is anaminoglycoside-aminocyclitol antibiotic isolated from a streptomycete,Streptomyces ribosidificus, originally identified in a soil sample fromTsu City of Mie Prefecture in Japan.[1] It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, andribose.[2] Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus[citation needed] and is considered a critically important antimicrobial by theWorld Health Organization.,[3][4] 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 bacterialribosomal RNAs.[5]
The biosynthesis of ribostamycin begins with the sugarD-glucose, which is phosphorylated at the 6 position to formglucose-6-phosphate. The enzyme rbmA contains a genetic sequence that corresponds toNAD+ binding and catalyzes the formation of 2-deoxy-scyllo-inosose. The enzyme rmbB then catalyzes the transamination of 2-deoxy-scyllo-inosose to 2-deoxy-scyllo-inosamine withL-glutamine andpyridoxal 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 withuridine 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 produceneamine. Neamine is then ribosylated to form ribostamycin.[2][3]
