Thienamycin
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IUPAC names
(5R,6S)-3-[(2-Aminoethyl)thio]-6-[(1R)-1-
hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept- 2-ene-2-carboxylic acid |
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3D model (Jmol)
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| C11H16N2O4S | |
| Molar mass | 272.32 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thienamycin also known as Thienpenem is one of the most potent naturally produced antibiotics known thus far, was discovered in Streptomyces cattleya in 1976. Thienamycin has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes. Thienamycin is a zwitterion at pH 7.
In 1976, fermentation broths obtained from the soil bacterium Streptomyces cattleya were found to be active in screens for inhibitors of peptidoglycan biosynthesis. Initial attempts to isolate the active species proved difficult due to the chemical instability of that component. After many attempts and extensive purification, the material was finally isolated in >90% purity, allowing for the structural elucidation of thienamycin in 1979 (Figure 1).
Thienamycin was the first among the naturally occurring class of carbapenem antibiotics to be discovered and isolated. Carbapenems are similar in structure to their antibiotic “cousins” the penicillins. Like penicillins, carbapenems contain a β-lactam ring (cyclic amide) fused to a five-membered ring. Carbapenems differ in structure from penicillins in that within the five-membered ring a sulfur is replaced by a carbon atom (C1) and an unsaturation is present between C2 and C3 in the five-membered ring.
In vitro, thienamycin employs a similar mode of action as penicillins through disrupting the cell wall synthesis (peptidoglycan biosynthesis) of various Gram-positive and Gram-negative bacteria (Staphylococcus aureus,Staphylococcus epidermidis, Pseudomonas aeruginosa to name a few). Although thienamycin binds to all of the penicillin-binding proteins (PBPs) in Escherichia coli, it preferentially binds to PBP-1 and PBP-2, which are both associated with the elongation of the cell wall.
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