TAN-1057A
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| Category | Antibiotics |
| Catalog number | BBF-02495 |
| CAS | 128126-44-3 |
| Molecular Weight | 355.4 |
| Molecular Formula | C13H25N9O3 |
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Description
TAN-1057A 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. It inhibited protein biosynthesis in Escherichia coli and S. aureus.
Specification
| Synonyms | Antibiotic TAN 1057A; TAN 1057A |
| IUPAC Name | (3S)-3-amino-N-[(5S)-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-YUMQZZPRSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Ribosomal alterations contribute to bacterial resistance against the dipeptide antibiotic TAN 1057
E Limburg, R Gahlmann, H-P Kroll, D Beyer Antimicrob Agents Chemother. 2004 Feb;48(2):619-22. doi: 10.1128/AAC.48.2.619-622.2004.
TAN 1057-resistant Staphylococcus aureus and Escherichia coli strains were selected to elucidate the mechanism of resistance and the mode of action of this dipeptide antibiotic. Cell-free translation with isolated ribosomes and S150 fractions from sensitive and resistant S. aureus strains demonstrated that alterations in the ribosomes contribute to the resistance of the bacteria.
2. Dihydropyrimidinones--a new class of anti-staphylococcal antibiotics
Michael Brands, Rainer Endermann, Reinhold Gahlmann, Jochen Krüger, Siegfried Raddatz Bioorg Med Chem Lett. 2003 Jan 20;13(2):241-5. doi: 10.1016/s0960-894x(02)00880-6.
We report the synthesis and pharmacological evaluation of new derivatives of natural dipeptide antibiotic TAN-1057 A, B. In the course of this program, we identified novel analogues of the natural product that display similar antibacterial activity and showed improved tolerability.
3. SAR studies on dihydropyrimidinone antibiotics
Lianhong Xu, Lijun Zhang, Robert Jones, Clifford Bryant, Nina Boddeker, Eric Mabery, Gina Bahador, Julia Watson, Jeffery Clough, Murty Arimilli, Wendy Gillette, Dorothy Colagiovanni, Keyu Wang, Craig Gibbs, Choung U Kim Bioorg Med Chem Lett. 2011 Mar 15;21(6):1670-4. doi: 10.1016/j.bmcl.2011.01.099. Epub 2011 Jan 31.
There is an urgent need for the development of novel antimicrobial agents that offer effective treatment against MRSA. Using a new class of dipeptide antibiotic TAN-1057A/B as lead, we designed, synthesized and evaluated analogs of TAN-1057A/B. Several novel dihydropyrimidinone antibiotics demonstrating comparable antibiotic efficacy while possessing favorable selectivity were identified.
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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 ╳
