Kirrothricin
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| Category | Antibiotics |
| Catalog number | BBF-01895 |
| CAS | 79190-00-4 |
| Molecular Weight | 780.98 |
| Molecular Formula | C44H64N2O10 |
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Description
Kirrothricin is originally isolated from Str. cinnamomeus Tu89. It has antibacterial action, but no activity to subtilis, Escherichia coli and fungi.
Specification
| Synonyms | 2H-Pyran-2-acetamide, N-((2E,4E,6S,7S,9S,10E,12E,14E,16E)-8,9-dihydroxy-6-methoxy-5,7,17-trimethyl-18-oxo-18-(1,2,5,6-tetrahydro-4-hydroxy-1-methyl-2-oxo-3-pyridinyl)-2,4-dihydroxy-5,5-dimethyl-6-((1E,3Z)-1,3-pentadienyl)-, (alphaS,2S,4S,6S)- |
| IUPAC Name | 2-[(2S,4S,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]oxan-2-yl]-N-[(2E,4E,10E,12E,14E,16E,18E)-8,9,18-trihydroxy-6-methoxy-5,7,17-trimethyl-18-(1-methyl-2,4-dioxopiperidin-3-ylidene)octadeca-2,4,10,12,14,16-hexaenyl]butanamide |
| Canonical SMILES | CCC(C(=O)NCC=CC=C(C)C(C(C)C(C(C=CC=CC=CC=C(C)C(=C1C(=O)CCN(C1=O)C)O)O)O)OC)C2(CC(C(C(O2)C=CC=CC)(C)C)O)O |
| InChI | InChI=1S/C44H64N2O10/c1-10-12-16-24-36-43(6,7)35(49)28-44(54,56-36)32(11-2)41(52)45-26-20-19-22-30(4)40(55-9)31(5)39(51)34(48)23-18-15-13-14-17-21-29(3)38(50)37-33(47)25-27-46(8)42(37)53/h10,12-24,31-32,34-36,39-40,48-51,54H,11,25-28H2,1-9H3,(H,45,52)/b12-10-,15-13+,17-14+,20-19+,23-18+,24-16+,29-21+,30-22+,38-37+/t31?,32?,34?,35-,36-,39?,40?,44-/m0/s1 |
| InChI Key | SUMCRDMQIVHXRY-XRAYCMFKSA-N |
Properties
| Appearance | Yellow Amorphous Powder |
| Boiling Point | 986.2°C at 760 mmHg |
| Melting Point | 100°C |
| Density | 1.178 g/cm3 |
Reference Reading
1. Natural kirromycin resistance of elongation factor Tu from the kirrothricin producer Streptomyces cinnamoneus
Carmela Cappellano, Federica Monti, Margherita Sosio, Stefano Donadio, Edoardo Sarubbi Microbiology (Reading). 1997 Feb;143 ( Pt 2):617-624. doi: 10.1099/00221287-143-2-617.
The antibiotic kirromycin (Kr) inhibits bacterial protein synthesis by binding to elongation factor Tu (EF-Tu). Streptomyces cinnamoneus and Nocardia lactamdurans, producers of antibiotics of the Kr class, are known to possess an EF-Tu resistant to Kr. Both micro-organisms appear to possess a single tuf gene and we have characterized the one from S. cinnamoneus, which belongs to the tuf1 family. To assess the molecular determinants of Kr resistance, the S. cinnamoneus tuf gene was expressed in Escherichia coli as a translational fusion to malE, which enabled the recovery by affinity chromatography of the recombinant protein uncontaminated by the host factor. The recombinant EF-Tu was able to catalyse polyU-directed polyPhe synthesis in two heterologous cell-free systems, even as an uncleaved fusion. When tested for antibiotic sensitivity it behaved like the natural S. cinnamoneus protein, showing equivalent resistance to Kr but sensitivity to the antibiotic GE2270, indicating that all the determinants for Kr resistance are intrinsic to the EF-Tu sequence. Multiple sequence analysis of EF-Tu proteins, together with knowledge of mutations conferring Kr resistance, allowed the identification of key residues as likely candidates for the natural Kr resistance of the S. cinnamoneus EF-Tu. One of these, Thr378, was mutated to the consensus Ala and the resulting mutant protein was sensitive to Kr. Interestingly, it retained some activity (30% of the control) even at high Kr concentrations.
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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 ╳
