N-Acetylthienamycin
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| Category | Antibiotics |
| Catalog number | BBF-03008 |
| CAS | 63701-32-6 |
| Molecular Weight | 314.36 |
| Molecular Formula | C13H18N2O5S |
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Description
It is produced by the strain of Streptomyces cattleya NRRL 8057. It is a broad-spectrum antibiotic, which has anti-gram-positive bacteria and gram-negative bacteria activity.
Specification
| Synonyms | Antibiotic 924A1; (5R,6S)-3-((2-acetamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethyl)thio)-6-(1-hydroxyethyl)-7-oxo-, (5R-(5-alpha,6-alpha(R*)))- |
| IUPAC Name | (5R,6S)-3-(2-acetamidoethylsulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCNC(=O)C)O |
| InChI | InChI=1S/C13H18N2O5S/c1-6(16)10-8-5-9(21-4-3-14-7(2)17)11(13(19)20)15(8)12(10)18/h6,8,10,16H,3-5H2,1-2H3,(H,14,17)(H,19,20)/t6-,8-,10-/m1/s1 |
| InChI Key | VUDXUIMGYZQRKK-GTNGPMTGSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 628.5°C at 760 mmHg |
| Density | 1.46 g/cm3 |
Reference Reading
1. Epithienamycins-novel beta-lactams related to thienamycin. I. Production and antibacterial activity
E O Stapley, P J Cassidy, J Tunac, R L Monaghan, M Jackson, S Hernandez, S B Zimmerman, J M Mata, S A Currie, D Daoust, D Hendlin J Antibiot (Tokyo). 1981 Jun;34(6):628-36. doi: 10.7164/antibiotics.34.628.
The epithienamycins are cell wall active antibiotics structurally related to N-acetylthienamycin. We have found forty-three isolated of Streptomyces flavogriseus which are capable of producing members of the epithienamycin family. Six major epithienamycin components, and xanthomycin, have been isolated from fermentation broth. Fermentation conditions can be varied to enrich for certain members of the epithienamycin family. All six components show activity in vitro versus a broad spectrum of bacterial species. The weight potencies vary 27 fold from the most active to least active.
2. Four enzymes define the incorporation of coenzyme A in thienamycin biosynthesis
Michael F Freeman, Kristos A Moshos, Micah J Bodner, Rongfeng Li, Craig A Townsend Proc Natl Acad Sci U S A. 2008 Aug 12;105(32):11128-33. doi: 10.1073/pnas.0804500105. Epub 2008 Aug 4.
The enzymatic activities of three proteins encoded by the thienamycin gene cluster of Streptomyces cattleya (ThnR, ThnH, and ThnT) have been shown to incrementally cleave CoA to afford the active side-chain component of the beta-lactam antibiotic thienamycin. These results supersede proposals based on earlier radiochemical incorporation experiments. For 20 years it has been thought that cysteine was directly incorporated into the antibiotic. Specific, stepwise truncation of CoA to 4-phosphopantetheine, pantetheine, and finally cysteamine was observed with ThnR, ThnH, and ThnT, respectively, in a series of coupled enzymatic assays. Pantetheinylated carbapenams were synthesized to address possible thienamycin biosynthetic intermediates and were shown to be effective substrates for the pantetheine-cleaving enzyme ThnT. Finally, a fourth gene, thnF, was shown to encode a protein capable of N-acetylating a model compound containing cysteamine in the presence of acetyl-CoA, consistent with the production of the S. cattleya cometabolite, N-acetylthienamycin. Taken together, these four enzymes are proposed to siphon CoA from primary metabolism to create the side chains for the predominant S. cattleya carbapenems, thienamycin and N-acetylthienamycin, in a process likely to be general for the broader class of these antibiotics.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
