TAN-1057B
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| Category | Antibiotics |
| Catalog number | BBF-02496 |
| CAS | 128126-45-4 |
| Molecular Weight | 355.4 |
| Molecular Formula | C13H25N9O3 |
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Description
TAN-1057B is an antibiotic produced by Flexibacter sp. PK-74 and PK-176. It is active against Gram-negative and Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus.
Specification
| Synonyms | Antibiotic TAN 1057B; TAN 1057B |
| IUPAC Name | (3S)-3-amino-N-[(5R)-2-(carbamoylamino)-6-oxo-4,5-dihydro-1H-pyrimidin-5-yl]-6-(diaminomethylideneamino)-N-methylhexanamide |
| Canonical SMILES | CN(C1CN=C(NC1=O)NC(=O)N)C(=O)CC(CCCN=C(N)N)N |
| InChI | InChI=1S/C13H25N9O3/c1-22(8-6-19-13(20-10(8)24)21-12(17)25)9(23)5-7(14)3-2-4-18-11(15)16/h7-8H,2-6,14H2,1H3,(H4,15,16,18)(H4,17,19,20,21,24,25)/t7-,8+/m0/s1 |
| InChI Key | ZMWBCGMRXBPXEU-JGVFFNPUSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Pyrimidinone antibiotics--heterocyclic analogues with improved antibacterial spectrum
Michael Brands, Yolanda Cancho Grande, Rainer Endermann, Reinhold Gahlmann, Jochen Krüger, Siegfried Raddatz Bioorg Med Chem Lett. 2003 Aug 18;13(16):2641-5. doi: 10.1016/s0960-894x(03)00578-x.
We report the synthesis and pharmacological evaluation of new derivatives of the natural dipeptide antibiotic TAN 1057 A,B containing heterocycles either in the beta-amino acid side chain or as mimics of the urea function. In the course of this program, we identified novel analogues that display activity towards a broader panel of Gram-positive bacteriae.
2. Novel antibiotics for the treatment of gram-positive bacterial infections
Michael Brands, Rainer Endermann, Reinhold Gahlmann, Jochen Krüger, Siegfried Raddatz, Jürgen Stoltefuss, Vladimir N Belov, Shamil Nizamov, Viktor V Sokolov, Armin de Meijere J Med Chem. 2002 Sep 12;45(19):4246-53. doi: 10.1021/jm0111191.
The natural dipeptide antibiotic TAN 1057 A,B displays excellent antibacterial activity against staphylococci including methicillin resistant Staphylococcus aureus. However, the in vitro activity against additional Gram-positive strains, in particular pneumococci and Enterococcus faecalis, proved to be considerably lower. We report the synthesis and pharmacological evaluation of new derivatives of this natural product that displayed increased antibacterial potency against staphylococci and were also active against pneumococci. In particular, the analogues bearing modified beta-homoarginine side chains with methylated guanidine moieties were shown to be significantly more potent than the natural product TAN 1057 A,B.
3. Characterization of a novel antibacterial agent that inhibits bacterial translation
Nina Böddeker, Gina Bahador, Craig Gibbs, Eric Mabery, John Wolf, Lianhong Xu, Julia Watson RNA. 2002 Sep;8(9):1120-8. doi: 10.1017/s1355838202024020.
Bacterial protein synthesis is the target for several classes of established antibiotics. This report describes the characterization of a novel translation inhibitor produced by the soil bacterium Flexibacter. The dipeptide antibiotic TAN1057 A/B was synthesized and designated GS7128. As reported previously, TAN1057 inhibits protein synthesis in both Escherichia coli and Staphylococcus aureus, leaving transcription unaffected. Cell-free translation systems from E. coli were used to further dissect the mechanism of translational inhibition. Binding of mRNA to ribosomes was unaffected by the drug, whereas the initiation reaction was reduced. Elongation of translation was completely inhibited by GS7128. Detailed analysis showed that the peptidyl transferase reaction was strongly inhibited, whereas tRNA binding to both A- and P-site was unaffected. Selection and analysis of drug-resistant mutants of S. aureus suggests that drug uptake may be mediated by a dipeptide transport mechanism.
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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 ╳
