Sisomicin

The starting material in the following synthesis is t-butyloxycarbonyl-L-aspartyl-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide designated (SM). 

Chemical Name 0-2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1 4)-0-(3-deoxy-4-C-methyl-3-(methylamino)-/3-L-arabinopyranosyl-(1 6)] -2-deoxy-D-strept-amine 

Trade Name Manufacturer Country Year Introduced 

Tank fermentation of Micromonospora inyoensis — Germination stage 1 Under aseptic conditions, add a lyophilized culture (or cells obtained from a slant culture) of M. inyoensis to a 300 ml shake flask containing 100 ml of the following sterile medium  

Incubate the flask and its contents for 5 days at 35°Cona rotary shaker (280 rpm, 2 stroke). 

Beef extract T ryptone Yeast extract Dextrose Starch 

The starting materiai in the foiiowing synthesis is t-butyioxycarbonyi-L-aspartyi-L-tyrosyl-L-methionyigiycyi-L-tryptophyi L-methionyi-L-aspartyi-L-phenyiaianine amide designated (SM). 

Chemical Name 0-2,6-diamino-2,3,4,6-tetradeoxy-Q -D-glycero-hex-4-enopyranosyl-(1- 4)- 

0-[3-deoxy-4-C-methyl-3-(methylamlno)-j3-L-arablnopyranosyl-(1- )l-2-deoxy-D-strept-amine 

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A Acetylation, O-Phosphorylation, and O-Adenylylation. A/-Acetylation, O-phosphorjiation, and O-adenyljiation provide mechanisms by which therapeutically valuable aminocyclitol antibiotics, eg, kanamycia [8063-07-8] gentamicin [1403-66-3] sisomicin [32385-11-8], streptomycia [57-92-1], neomycin, or spectinomycin are rendered either partially or completely iaactive. Thus, eg, kanamycia B [4696-78-8] (50) can be iaactivated by modification at several sites, as shown. The elucidation of these mechanisms has allowed chemical modification of the sites at which the iaactivation occurs. Several such bioactive analogues, eg, dibekacia and amikacin have been prepared and are not subject to the iaactivation hence, they inhibit those organisms against which the parent antibiotics are iaeffective (96) (see Antibacterial agents, synthetic). 

Among the older aminoglycoside derivatives, kanamycin A and sisomicin were, at one time, a significant part of medical practice, but have now been largely replaced by the compounds Hsted in Table 1. Streptomycin is stiH used in a few restricted situations. 

To a solution of 5 g of sisomicin in 250 ml of water add 1 N sulfuric acid until the pH of the solution is adjusted to about 5. To the solution of sisomicin sulfuric acid addition salt thereby formed, add 2 ml of acetaldehyde, stir for 10 minutes, then add 0.B5 g of sodium cyanoborohydride. Continue stirring at room temperature for 15 minutes, then concentrate solution In vacuo to a volume of about 100 ml, treat the solution with a basic ion exchange resin [e.g., Amberlite IRA401S (OH )], then lyophilize to a residue comprising 1-N-ethyl-sisomicin. 

Soybean meal, by fermentation Bacitracin Clavulanic acid Cycloserine Erythromycin Gentamicin sulfate Kanamycin sulfate Micronomicin Novobiocin Oleandomycin Oxamniquine Oxytetracycline Paromomycin Ribostamicin Sisomicin... 

Exsel -Selenium sulfide Extencilline - Penicillin G benzathine Extendryl - Phenylephrine HCI Extracort - Triamcinolone acetonide Extramycin -Sisomicin Extranase - Bromelain Extren - Aspirin... 

Sisomicin Tobramydn Livldomycins A and B Paromomydn Ribostamydn Amikadn 6 -W-Acetyl derivatives of the respective substrates Providencia spp. Providencia spp. Pseudomonas aeruginosa... 

The hydroxy groups in natural products like, for example, the macrolide antibiotics erythromycin, 1"1 and desmycosin, 2001 2011 as well as the 3-(hydroxymethyl)-2- or 3-cephems 2021 and derivatives of the amino sugar garamin 2031 have been converted into the carbamate function with CDI and amines. In the case of aminoglycoside antibiotics of the sisomicin series, thiocarbamates or dithiocarbamates have been prepared from alcohols or thiols using ImCSIm and amines.12041... 

The primary application of RIA for antibiotics has been in the medical area, and primarily for antibiotics not used in agriculture. Assays have been developed for gentamicin tobramycin, sisomicin, netilmicin and for hygromycin B, an antibiotic used primarily in agriculture (36-37, 22-24). Gentamycin could be measured as low as 80 pg, tobramycin 280 pg, netilmicin 300 pg mL. 

A, amikacin Ap, apramycin B, butirosin D, dibekacin G, gentamicin H, hygromycin I, isepam-icin K, kanamycin L, lividomycin N, netilmicin Ne, neomycin P, paromomycin R, ribostamycin S, sisomicin Sp, spectinomycin St, streptomycin T, tobramycin. 

This enzyme [EC 2.7.7.46] catalyzes the reaction of a nucleoside triphosphate with gentamicin to produce a 2"-nucleotidylgentamicin and pyrophosphate (or, diphosphate). The nucleoside triphosphate can be ATP, dATP, CTP, ITP, or GTP. Kanamycin, tobramycin, and sisomicin can also act as the acceptor substrate. The nucleotidyl residue is transferred to the 2-hydroxyl group of the 3-amino-3-deoxy-D-glucose moiety in the acceptor substrate. 

The aminoglycosides include streptomycin, gentamicin, tobramycin, netilmicin, kanamycin, amikacin, sisomicin, neomycin, paromomycin and others. Those are bactericidal antibiotics. This bactericidal activity is concentration dependent in contrast to the... 

The aminoglycosides include streptomycin, neomycin, kanamycin, amikacin, gentamicin, tobramycin, sisomicin, netilmicin, and others. They are used most widely against gram-negative enteric bacteria, especially in bacteremia and sepsis, in combination with vancomycin or a penicillin for endocarditis, and for treatment of tuberculosis. 

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