89139-42-4

Basic information

• Product Name: teicoplanin aglycone
• Synonyms: teicoplanin aglycone
• CAS NO: 89139-42-4
• Molecular Formula: C₅₈H₄₅Cl₂N₇O₁₈
• Molecular Weight: 1198.93
• Mol File: 89139-42-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: teicoplanin aglycone(CAS DataBase Reference)
• NIST Chemistry Reference: teicoplanin aglycone(89139-42-4)
• EPA Substance Registry System: teicoplanin aglycone(89139-42-4)

Safety Data

• Hazardous Substances Data: 89139-42-4(Hazardous Substances Data)

Usage

General Description

Teicoplanin aglycone is a glycopeptide antibiotic that is derived from the fermentation of Actinoplanes teichomyceticus. It is a complex molecule consisting of a heptapeptide core attached to a glycosylated moiety. Teicoplanin aglycone is a powerful antibiotic that works by inhibiting bacterial cell wall synthesis, making it effective against a wide range of Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). It is often used in the treatment of serious infections, such as osteomyelitis, endocarditis, and sepsis, and is particularly valuable for its long half-life and once-daily dosing. However, it is not commonly used due to its high cost and potential for adverse effects, including nephrotoxicity and ototoxicity.

Upstream product

• 91032-39-2 C₆₆H₅₈Cl₂N₈O₂₃ 

Downstream Products

• 562105-40-2 C₆₉H₆₂Cl₂N₈O₁₈ 
• 104581-77-3 C₆₃H₅₃Cl₂N₇O₂₀ 
• 117226-75-2 C₅₈H₄₄Cl₂N₆O₁₈ 
• 733810-59-8 C₆₄H₅₆Cl₂N₈O₂₂ 
• 122172-99-0 C₆₄H₅₉Cl₂N₉O₁₇ 

Relevant articles and documents

Role of the carbohydrate moieties in chiral recognition on teicoplanin- based LC stationary phases

For this study, we used the macrocyclic antibiotic teicoplanin, a molecule consisting of an aglycone peptide 'basket' with three attached carbohydrate (sugar) moieties. The sugar units were removed and the aglycone was purified. Two chiral stationary phases (CSPs) were prepared in a similar way, one with the native teicoplanin molecule and the other with the aglycone. Twenty-six compounds were evaluated on the two CSPs with seven RPLC mobile phases and two polar organic mobile phases. The compounds were 13 amino acids or structurally related compounds (including DOPA, folinic acid, etc.) and 13 other compounds (such as carnitine, bromacil, etc.). The chromatographic results are given as the retention, selectivity, and resolution factors along with the peak efficiency and the enantioselective free energy difference corresponding to the separation of the two enantiomers. The polarities of the two CSPs are similar. It is clearly established that the aglycone is responsible for the enantioseparation of amino acids. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP was between 0.3 and 1 kcal/mol for amino acid enantioseparations. This produced resolution factors 2-5 times higher with the aglycone CSP. Four non amino acid compounds were separated only on the teicoplanin CSP. Six and five compounds were better separated on the teicoplanin and aglycone CSPs, respectively. Although the sugar units decrease the resolution of α-amino acid enantiomers, they can contribute significantly to the resolution of a number of non amino acid enantiomeric pairs.

Total synthesis of teicoplanin aglycon

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Total synthesis of the teicoplanin aglycon [16]

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