35834-26-5

Usage

Uses

Used in Pharmaceutical Industry:
ROSAMICIN is used as an antibiotic for treating and preventing infections caused by the aforementioned bacterial strains. Its effectiveness in combating these pathogens makes it a valuable asset in the fight against bacterial infections.
Used in Medical Research:
In addition to its direct application as an antibiotic, ROSAMICIN may also be used in medical research to study the mechanisms of antibiotic resistance and the development of new drugs to combat resistant strains. Its activity against specific bacteria can provide insights into the design of novel therapeutic agents.
Used in Diagnostics:
ROSAMICIN may also be utilized in diagnostic applications to identify and differentiate between various bacterial infections. Its specificity for certain bacterial strains can aid in the accurate diagnosis of infections, enabling targeted and effective treatment plans.

Biochem/physiol Actions

Macrolide antibiotic similar to erythromycin, and with a similar spectrum of bactericidal activity. Against a wide variety of anaerobes, rosamicin is at least as potent as, and in some cases more potent than, erythromycin.

InChI:InChI=1/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20?,21+,22+,24-,25?,27-,28-,29?,30+,31+/m1/s1

Upstream product

• 102438-11-9 rosaramicin N-oxide 
• 1403991-98-9 (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one 
• 635758-46-2 (S)-3-((E)-2-methylpent-2-enoyl)-4-benzyloxazolidin-2-one 
• 56689-42-0 12,13-de-epoxy-12,13-didehydrorosaramicin 
• 58947-83-4 12,13-de-epoxy-12,13-dehydro-20-dihydrorosaramicin 
• 59227-83-7 12,13-de-epoxy-12,13-didehydro-20-deoxorosaramicin 
• 74758-60-4 protylonolide 
• 16957-70-3 2-methylpent-2-enoic acid 
• 219610-75-0 (S)-2-((benzyloxy)methyl)butan-1-ol 
• 163457-34-9 (+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone 
• 102518-92-3 (4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enal 

Downstream Products

• 61486-91-7 12,13-de-epoxy-12,13-didehydrorosamicin 20-dimethyl acetal 
• 56689-42-0 12,13-de-epoxy-12,13-didehydrorosaramicin 
• 112389-32-9 20-deoxorosaramicin-20-diphenylthioacetal 
• 112389-33-0 11(R)-20-deoxo-10,11-dihydro-11-phenylthiorosaramicin 20-diphenylthioacetal 

Relevant academic research and scientific papers

Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization

Polyketide synthases (PKSs) represent a powerful catalytic platform capable of effecting multiple carbon-carbon bond forming reactions and oxidation state adjustments. We explored the functionality of two terminal PKS modules that produce the 16-membered tylosin macrocycle, using them as biocatalysts in the chemoenzymatic synthesis of tylactone and its subsequent elaboration to complete the first total synthesis of the juvenimicin, M-4365, and rosamicin classes of macrolide antibiotics via late-stage diversification. Synthetic chemistry was employed to generate the tylactone hexaketide chain elongation intermediate that was accepted by the juvenimicin (Juv) ketosynthase of the penultimate JuvEIV PKS module. The hexaketide is processed through two complete modules (JuvEIV and JuvEV) in vitro, which catalyze elongation and functionalization of two ketide units followed by cyclization of the resulting octaketide into tylactone. After macrolactonization, a combination of in vivo glycosylation, selective in vitro cytochrome P450-mediated oxidation, and chemical oxidation was used to complete the scalable construction of a series of macrolide natural products in as few as 15 linear steps (21 total) with an overall yield of 4.6%.

Semisynthetic Macrolide Antibacterials Derived from Tylosin. Synthesis of 3-O-Acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin and Related Compounds, as well as the 12,13-Epoxy Derivatives

Selective acylation techniques have been developed that enable the synthesis of 3-O-acetyl-4''-O-isovaleryltylosin and 3-O-acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin to be carried out in an efficient manner starting from tylosin.The syntheses of the 2'-O-acetyl, 23-O-acetyl, and 2',23-di-O-acetyl derivatives of the latter are also described.The synthesis of key hydrazones is also described.The regio- and stereo-selective epoxidation of tylosin and its acyl derivatives afforded the 12,13-epoxyanalogues, which were used to synthesize novel acylated 12,13-epoxy derivatives of 23-O-demycinosyltylosin.