Sisomicin

Base Information

• Chemical Name: Sisomicin
• CAS No.: 32385-11-8
• Deprecated CAS: 34406-63-8,37332-59-5,53179-08-1
• Molecular Formula: C19H37N5O7
• Molecular Weight: 447.532
• European Community (EC) Number: 251-018-2
• UNII: X55XSL74YQ
• Nikkaji Number: J342.544D
• Wikipedia: Sisomicin
• Wikidata: Q3962119
• NCI Thesaurus Code: C72569
• Metabolomics Workbench ID: 53436
• ChEMBL ID: CHEMBL221886
• Mol file: 32385-11-8.mol

Synonyms:4,5 Dehydrogentamicin;4,5-Dehydrogentamicin;Antibiotic 6640;Extramycin;Pathomycin;Rickamicin;Sch 13475;Sch-13475;Sch13475;Siseptin;Sisomicin;Sisomicin Sulfate;Sisomicin Sulfate (2:5) Salt;Sisomycin;Sissomicin;Sizomycin

Chemical Property of Sisomicin

Chemical Property:

• Vapor Pressure: 1.79E-30mmHg at 25°C
• Melting Point: 80-93°C
• Refractive Index: 1.7600 (estimate)
• Boiling Point: 676.579 °C at 760 mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 362.982 °C
• PSA: 296.70000
• Density: 1.387 g/cm³
• LogP: -0.23140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly,
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 447.26929854
• Heavy Atom Count: 31
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

Sisomicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CC=C(O3)CN)N)N)N)O
• Isomeric SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N)N)O
• Recent ClinicalTrials: Sisomicin Cream Vs Nadifloxacin Cream in Primary Pyodermas (Study P04460)
• General Description: Sisomicin is an aminoglycoside antibiotic that can be biotransformed by *Micromonospora sagamiensis* into other clinically relevant antibiotics, such as gentamicin CIa and sagamicin. This bioconversion highlights its role as a precursor in the biosynthesis of structurally related compounds, demonstrating its metabolic versatility. The process involves specific enzymatic activities, including (4',5')-reduction, which distinguishes *M. sagamiensis* from other *Micromonospora* species lacking this capability. These findings underscore the potential of sisomicin in antibiotic development through microbial transformation.

Technology Process of Sisomicin

There total 10 articles about Sisomicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

sisomicin hemipentasulfate → sisomicin (32385-11-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 5h; Reagent/catalyst;

Reference yield: 92.0%

Sisomicin sulfate (53179-09-2,53776-71-9,68231-64-1) → sisomicin (32385-11-8)

Guidance literature:

With activated anion exchange resin (amberlite 4200 Cl); In methanol; at 15 - 20 ℃; for 18h; Inert atmosphere;

Reference yield: 10.0%

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide (66567-31-5) → sisomicin (32385-11-8) + 1-deamino-1-hydroxysisomicin (66065-95-0,66101-45-9) + netilmicin (56391-56-1) + 1-epi-N-ethylsisomicin (67650-39-9)

Guidance literature:

With sodium hydroxide; for 50h; Further byproducts given; Heating;

DOI:10.1039/P19810002168

upstream raw materials:

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide

N-[(1S,2R,3R,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide

3,2',6'-tri-N-acetyl-1-deamino-1-oxosisomicin

3,2',6'-tri-N-acetylsisomicin

Downstream raw materials:

Gentamicin C1a

micronomicin

Sisamin

3,2',6'-tri-N-acetylsisomicin

Refernces

Biotransformation of sisomicin and verdamicin by Micromonospora sagamiensis

10.1080/00021369.1982.10865090

The research investigates the biotransformation of sisomicin and verdamicin by Micromonospora sagamiensis. The study found that the resting cells of a 2-deoxystreptamine idiotrophic mutant of M. sagamiensis could transform sisomicin into gentamicin CIa and sagamicin, while verdamicin was transformed into gentamicin C2a, C2, and then CI. The biotransformation products were isolated using ion exchange and carbon column chromatographic procedures and identified through various analytical techniques. The study also compared the biotransformation capabilities of other Micromonospora species, such as M. zionensis and M. inyoensis, and found that they lacked the (4',5')-reduction activity present in M. sagamiensis. Instead, M. zionensis transformed sisomicin into antibiotic G-52 and verdamicin into a new antibiotic, VF3-1, which was suggested to be 6'-N-methylverdamicin based on chromatographic and mass spectrum data. The findings provide insights into the biosynthetic pathways of these antibiotics and their potential for further development.