CAS 50935-71-2

Kirromycin

Description:

Kirromycin is an antibiotic compound that belongs to the class of macrolides, specifically known for its activity against certain bacterial strains. It is produced by the bacterium *Micromonospora purpurea* and exhibits a unique mechanism of action by inhibiting protein synthesis in bacteria. Kirromycin binds to the ribosomal subunit, interfering with the translocation step during translation, which ultimately halts bacterial growth. This compound is characterized by its complex macrolide structure, which includes a large lactone ring and various functional groups that contribute to its biological activity. Kirromycin has been studied for its potential therapeutic applications, particularly in treating infections caused by Gram-positive bacteria. However, its clinical use is limited due to the development of resistance and the availability of more effective antibiotics. As with many antibiotics, the understanding of kirromycin's pharmacokinetics, toxicity, and resistance mechanisms continues to evolve, making it a subject of interest in microbiological and pharmaceutical research.

Formula: C₄₃H₆₀N₂O₁₂

InChI: InChI=1S/C43H60N2O12/c1-9-11-13-21-31-42(6,7)38(50)39(51)43(54,57-31)28(10-2)40(52)44-23-17-16-19-26(4)36(55-8)27(5)37-35(49)34(48)30(56-37)20-15-12-14-18-25(3)33(47)32-29(46)22-24-45-41(32)53/h9,11-22,24,27-28,30-31,34-39,48-51,54H,10,23H2,1-8H3,(H,44,52)(H2,45,46,53)/b11-9-,14-12+,17-16+,20-15+,21-13+,25-18+,26-19+/t27-,28-,30-,31+,34+,35+,36-,37+,38+,39-,43-/m1/s1

InChI key: InChIKey=HMSYAPGFKGSXAJ-PAHGNTJYSA-N

SMILES: [C@H](C(NC/C=C/C=C(/[C@H]([C@@H](C)[C@@]1(O[C@H](/C=C/C=C/C=C(/C(=O)C2=C(O)C=CNC2=O)\C)[C@H](O)[C@@H]1O)[H])OC)\C)=O)(CC)[C@@]3(O)O[C@@H](/C=C/C=C\C)C(C)(C)[C@@H](O)[C@H]3O

Synonyms:

• (2R)-N-[(2E,4E,6R)-7-[(2S,5R)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(2-hydroxy-4-oxo-1H-pyridin-3-yl)-6-methyl-7-oxo-hepta-1,3,5-trienyl]tetrahydrofuran-2-yl]-6-methoxy-5-methyl-octa-2,4-dienyl]-2-[2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]tetrahydropyran-2-yl]butanamide
• (2S)-N-[(6S,7R)-7-{(2S,3S,4R,5R)-3,4-dihydroxy-5-[7-(2-hydroxy-4-oxo-1,4-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]tetrahydrofuran-2-yl}-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-[(2R,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-(penta-1,3-dien-1-yl)tetrahydro-2H-pyran-2-yl]butanamide (non-preferred name)
• (αS,2R,3R,4R,6S)-N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-Dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-2H-pyran-2-acetamide
• 2H-Pyran-2-acetamide, N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-, (αS,2R,3R,4R,6S)-
• 2H-Pyran-2-acetamide, N-[(2E,4E,6S,7R)-7-[(2S,3S,4R,5R)-5-[(1E,3E,5E)-7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrienyl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadienyl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3Z)-1,3-pentadienyl]-, (αS,2R,3R,4R,6S)-
• 2H-Pyran-2-acetamide, N-[7-[5-[7-(1,2-dihydro-4-hydroxy-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrienyl]tetrahydro-3,4-dihydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadienyl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1,3-pentadienyl)-, [2R-[2α,2[S*[2E,4E,6S*,7R*[2S*,3S*,4R*,5R*(1E,3E,5E)]]],3β,4β,6β(1E,3E)]]-
• Delvomycin
• Kirromycin
• Mocimycin
• N-[(2E,4E)-7-{3,4-dihydroxy-5-[(1E,3E,5E)-7-(2-hydroxy-4-oxo-1,4-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]tetrahydrofuran-2-yl}-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-{2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dien-1-yl]tetrahydro-2H-pyran-2-yl}butanamide (non-preferred name)
• NSC 316094

Kirromycin

CAS: 50935-71-2

Formula: C₄₃H₆₀N₂O₁₂

Purity: ≥ 96.0%

Color and Shape: Yellow powder

Molecular weight: 796.94

Ref: 7W-GA9046

Kirromycin

CAS: 50935-71-2

Formula: C₄₃H₆₀N₂O₁₂

Molecular weight: 796.96

Ref: 4Z-K-027001

Kirromycin from Streptomyces collinus

CAS: 50935-71-2

Kirromycin is a hydroxylated tetracycline antibiotic that inhibits protein synthesis. It is used as a chemotherapeutic treatment against microbial infections, and has been shown to be effective against Streptomyces collinus. Kirromycin is also an inhibitor of bacterial ribosome activity, which can lead to the death of bacteria. This compound binds to the 30S subunit of the ribosome and prevents the attachment of amino acids to the nascent polypeptide chain during protein synthesis. The antibiotic thiostrepton from Streptomyces collinus was found to inhibit both growth and antibiotic resistance in Saccharomyces cerevisiae strains.

Formula: C₄₃H₆₀N₂O₁₂

Purity: Min. 95%

Molecular weight: 796.94 g/mol

Ref: 3D-ACA93571