Ribostamycin

Ribostamycin
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	J01GB10 ( WHO );
Identifiers
	IUPAC name (1R,2R,3S,4R,6S)-4,6-diamino-3-hydroxy-2-(β-D-ribofuranosyloxy)cyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside;
CAS Number	25546-65-0 ; 53797-35-6 (sulfate);
PubChem CID	33042 ;
ChemSpider	30581 ;
UNII	2Q5JOU7T53 ;
ChEMBL	ChEMBL221572 ;
CompTox Dashboard (EPA)	DTXSID6048541 ;
ECHA InfoCard	100.053.421
Chemical and physical data
Formula	C17H34N4O10
Molar mass	454.477 g·mol−1
3D model (JSmol)	Interactive image ;
	SMILES C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)O)N;
	InChI InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1 ; Key:NSKGQURZWSPSBC-VVPCINPTSA-N ;
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Last updated November 15, 2024

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.^[1] It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, and ribose.^[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 the World 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 bacterial ribosomal RNAs.^[5]

Biosynthesis

The biosynthesis of ribostamycin begins with the sugar D-glucose, which is phosphorylated at the 6 position to form glucose-6-phosphate. The enzyme rbmA contains a genetic sequence that corresponds to NAD⁺ 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 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.^[2]^[3]

Related Research Articles

Neomycin is an aminoglycoside antibiotic that displays bactericidal activity against Gram-negative aerobic bacilli and some anaerobic bacilli where resistance has not yet arisen. It is generally not effective against Gram-positive bacilli and anaerobic Gram-negative bacilli. Neomycin comes in oral and topical formulations, including creams, ointments, and eyedrops. Neomycin belongs to the aminoglycoside class of antibiotics that contain two or more amino sugars connected by glycosidic bonds.

<span class="mw-page-title-main">Gentamicin</span> Antibiotic medication

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Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms.

Novobiocin, also known as albamycin, is an aminocoumarin antibiotic that is produced by the actinomycete Streptomyces niveus, which has recently been identified as a subjective synonym for S. spheroides a member of the class Actinomycetia. Other aminocoumarin antibiotics include clorobiocin and coumermycin A1. Novobiocin was first reported in the mid-1950s.

<span class="mw-page-title-main">Spectinomycin</span> Antibiotic

Spectinomycin, sold under the tradename Trobicin among others, is an antibiotic useful for the treatment of gonorrhea infections. It is given by injection into a muscle.

<span class="mw-page-title-main">Neocarzinostatin</span> Chemical compound

Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus.

<span class="mw-page-title-main">Tunicamycin</span> Chemical compound

Tunicamycin is a mixture of homologous nucleoside antibiotics that inhibits the UDP-HexNAc: polyprenol-P HexNAc-1-P family of enzymes. In eukaryotes, this includes the enzyme GlcNAc phosphotransferase (GPT), which catalyzes the transfer of N-acetylglucosamine-1-phosphate from UDP-N-acetylglucosamine to dolichol phosphate in the first step of glycoprotein synthesis. Tunicamycin blocks N-linked glycosylation (N-glycans) and treatment of cultured human cells with tunicamycin causes cell cycle arrest in G1 phase. It is used as an experimental tool in biology, e.g. to induce unfolded protein response. Tunicamycin is produced by several bacteria, including Streptomyces clavuligerus and Streptomyces lysosuperificus.

The enzyme dTDP-glucose 4,6-dehydratase (EC 4.2.1.46) catalyzes the chemical reaction

In enzymology, a glutamine-scyllo-inositol transaminase is an enzyme that catalyzes the chemical reaction

In enzymology, a scyllo-inosamine 4-kinase is an enzyme that catalyzes the chemical reaction

The aminocyclitols are compounds related to cyclitols. They possess features of relative and absolute configuration that are characteristic of their class and have been extensively studied; but these features are not clearly displayed by general methods of stereochemical nomenclature, so that special methods of specifying their configuration are justified and have long been used. In other than stereochemical respects, their nomenclature should follow the general rules of organic chemistry.

The Aminoshikimate pathway is a biochemical pathway present in some plants, which has been studied by biologists, biochemists and especially those interested in manufacture of novel antibiotic drugs. The pathway is a novel variation of the shikimate pathway. The aminoshikimate pathway was first discovered and studied in the rifamycin B producer Amycolatopsis mediterranei. Its end product, 3-amino-5-hydroxybenzoate, serves as an initiator for polyketide synthases in the biosynthesis of ansamycins.

<span class="mw-page-title-main">Nogalamycin</span> Chemical compound

Nogalamycin is an anthracycline antibiotic produced by the soil bacteria Streptomyces nogalater. It has antitumor properties but it is also highly cardiotoxic. The less cardiotoxic semisynthetic analog menogaril was developed in the 1970s. Currently nogalamycin and menogaril are not used clinically.

Thymidine diphosphate glucose is a nucleotide-linked sugar consisting of deoxythymidine diphosphate linked to glucose. It is the starting compound for the syntheses of many deoxysugars.

2-deoxy-scyllo-inosamine dehydrogenase (EC 1.1.1.329, neoA (gene name), kanK (gene name)) is an enzyme with systematic name 2-deoxy-scyllo-inosamine:NAD(P)⁺ 1-oxidoreductase. This enzyme catalyses the following chemical reaction

Paromamine 6'-oxidase (EC 1.1.3.43, btrQ (gene), neoG (gene), kanI (gene), tacB (gene)) is an enzyme with systematic name paromamine:oxygen 6'-oxidoreductase. This enzyme catalyses the following chemical reaction

2-deoxy-scyllo-inosamine dehydrogenase (SAM-dependent) is an enzyme with systematic name 2-deoxy-scyllo-inosamine:S-adenosyl-L-methionine 1-oxidoreductase. This enzyme catalyses the following chemical reaction

Neamine transaminase is an enzyme with systematic name neamine:2-oxoglutarate aminotransferase. This enzyme catalyses the following chemical reaction

2-deoxy-scyllo-Inosose synthase is an enzyme with systematic name D-glucose-6-phosphate phosphate-lyase (2-deoxy-scyllo-inosose-forming). This enzyme catalyses the following chemical reaction

C-1027 or lidamycin is an antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein. It shows antibiotic activity against most Gram-positive bacteria. It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

References

↑ Shomura T, Ezaki N, Tsuruoka T, Niwa T, Akita E (March 1970). "Studies on antibiotic SF-733, a new antibiotic. I. Taxonomy, isolation and characterization". The Journal of Antibiotics. 23 (3): 155–61. doi: 10.7164/antibiotics.23.155 . PMID 5453309.
1 2 Subba B, Kharel MK, Lee HC, Liou K, Kim BG, Sohng JK (August 2005). "The ribostamycin biosynthetic gene cluster in Streptomyces ribosidificus: comparison with butirosin biosynthesis". Molecules and Cells. 20 (1): 90–6. doi:10.1016/S1016-8478(23)13203-1. PMID 16258246.
1 2 Kurumbang NP, Liou K, Sohng JK (February 2011). "Biosynthesis of ribostamycin derivatives by reconstitution and heterologous expression of required gene sets". Applied Biochemistry and Biotechnology. 163 (3): 373–82. doi:10.1007/s12010-010-9045-6. PMID 20676801. S2CID 22366703.
↑ WHO Advisory Group on Integrated Surveillance of Antimicrobial Resistance (AGISAR) (2011). Critically Important Antimicrobials for Human Medicine (PDF) (Report) (3rd revision ed.). World Health Organization. ISBN 978-92-4-150448-5.
↑ Kudo F, Eguchi T (September 2009). "Biosynthetic genes for aminoglycoside antibiotics". The Journal of Antibiotics. 62 (9): 471–81. doi: 10.1038/ja.2009.76 . PMID 19644520. S2CID 41969498.

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[pmid5453309-1] Shomura T, Ezaki N, Tsuruoka T, Niwa T, Akita E (March 1970). "Studies on antibiotic SF-733, a new antibiotic. I. Taxonomy, isolation and characterization". The Journal of Antibiotics. 23 (3): 155–61. doi: 10.7164/antibiotics.23.155 . PMID 5453309.

[Subba-2] 1 2 Subba B, Kharel MK, Lee HC, Liou K, Kim BG, Sohng JK (August 2005). "The ribostamycin biosynthetic gene cluster in Streptomyces ribosidificus: comparison with butirosin biosynthesis". Molecules and Cells. 20 (1): 90–6. doi:10.1016/S1016-8478(23)13203-1. PMID 16258246.

[Kurumbang-3] 1 2 Kurumbang NP, Liou K, Sohng JK (February 2011). "Biosynthesis of ribostamycin derivatives by reconstitution and heterologous expression of required gene sets". Applied Biochemistry and Biotechnology. 163 (3): 373–82. doi:10.1007/s12010-010-9045-6. PMID 20676801. S2CID 22366703.

[4] WHO Advisory Group on Integrated Surveillance of Antimicrobial Resistance (AGISAR) (2011). Critically Important Antimicrobials for Human Medicine (PDF) (Report) (3rd revision ed.). World Health Organization. ISBN 978-92-4-150448-5.

[pmid19644520-5] Kudo F, Eguchi T (September 2009). "Biosynthetic genes for aminoglycoside antibiotics". The Journal of Antibiotics. 62 (9): 471–81. doi: 10.1038/ja.2009.76 . PMID 19644520. S2CID 41969498.

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