Thiocillin I
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| Category | Antibiotics |
| Catalog number | BBF-04307 |
| CAS | 59979-01-0 |
| Molecular Weight | 1160.37 |
| Molecular Formula | C48H49N13O10S6 |
| Purity | >95% by HPLC |
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Description
It is the simplest of the macrocyclic thiazole peptide antibiotic first isolated from bacillus badius and bacillus cereus. It has anti-gram-positive bacteria activity.
Specification
| Synonyms | 44-O-Demethylthiocillin II; G-15-II; 2'-[(11S,14Z,21S,28S)-14-ethylidene-9,10,11,12,13,14,20,21,27,28-decahydro-11,28-bis[(1R)-1-hydroxyethyl]-21-(1-hydroxy-1-methylethyl)-9,12,19,26-tetraoxo-19H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-N-[(1Z)-1-[[[(2R)-2-hydroxypropyl]amino]carbonyl]-1-propen-1-yl]-[2,4'-bithiazole]-4-carboxamide |
| Storage | Store at -20°C |
| IUPAC Name | 2-[2-[(12S,19S,26Z,29S)-26-ethylidene-12,29-bis[(1R)-1-hydroxyethyl]-19-(2-hydroxypropan-2-yl)-14,21,28,31-tetraoxo-10,17,24,34-tetrathia-6,13,20,27,30,35,36,37,38-nonazahexacyclo[30.2.1.18,11.115,18.122,25.02,7]octatriaconta-1(35),2(7),3,5,8,11(38),15,18(37),22,25(36),32-undecaen-5-yl]-1,3-thiazol-4-yl]-N-[(Z)-1-[[(2R)-2-hydroxypropyl]amino]-1-oxobut-2-en-2-yl]-1,3-thiazole-4-carboxamide |
| Canonical SMILES | CC=C1C2=NC(=CS2)C(=O)NC(C3=NC(=CS3)C(=O)NC(C4=NC(=CS4)C5=C(C=CC(=N5)C6=NC(=CS6)C7=NC(=CS7)C(=O)NC(=CC)C(=O)NCC(C)O)C8=NC(=CS8)C(=O)NC(C(=O)N1)C(C)O)C(C)O)C(C)(C)O |
| InChI | InChI=1S/C48H49N13O10S6/c1-8-23(36(65)49-12-19(3)62)51-37(66)27-15-74-45(56-27)31-18-75-44(58-31)25-11-10-22-34(50-25)26-13-76-46(53-26)33(21(5)64)60-39(68)29-17-77-47(57-29)35(48(6,7)71)61-40(69)30-16-73-43(55-30)24(9-2)52-41(70)32(20(4)63)59-38(67)28-14-72-42(22)54-28/h8-11,13-21,32-33,35,62-64,71H,12H2,1-7H3,(H,49,65)(H,51,66)(H,52,70)(H,59,67)(H,60,68)(H,61,69)/b23-8-,24-9-/t19-,20-,21-,32+,33+,35-/m1/s1 |
| InChI Key | FEORQDDAQBRWPT-RJFXJIJJSA-N |
| Source | Bacillus sp. |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.456 g/cm3 |
| Solubility | Soluble in THF, Ethanol, Methanol, DMF, DMSO, Chloroform, Acetone; Poorly soluble in Water |
Reference Reading
1. Thiazolyl peptide antibiotic biosynthesis: a cascade of post-translational modifications on ribosomal nascent proteins
Christopher T Walsh, Michael G Acker, Albert A Bowers J Biol Chem . 2010 Sep 3;285(36):27525-31. doi: 10.1074/jbc.R110.135970.
Antibiotics of the thiocillin, GE2270A, and thiostrepton class, which block steps in bacterial protein synthesis, contain a trithiazolyl (tetrahydro)pyridine core that provides the architectural constraints for high affinity binding to either the 50 S ribosomal subunit or elongation factor Tu. These mature antibiotic scaffolds arise from a cascade of post-translational modifications on 50-60-residue prepeptide precursors that trim away the N-terminal leader sequences (approximately 40 residues) while the C-terminal 14-18 residues are converted into the mature scaffold. In the producing microbes, the genes encoding the prepeptide open reading frames are flanked in biosynthetic clusters by genes encoding post-translational modification enzymes that carry out lantibiotic-type dehydrations of Ser and Thr residues to dehydroamino acid side chains, cyclodehydration and oxidation of cysteines to thiazoles, and condensation of two dehydroalanine residues en route to the (tetrahydro)pyridine core. The trithiazolyl pyridine framework thus arises from post-translational modification of the peptide backbone of three Cys and two Ser residues of the prepeptide.
2. Investigations into PoyH, a promiscuous protease from polytheonamide biosynthesis
Maximilian J Helf, Jörn Piel, Michael F Freeman J Ind Microbiol Biotechnol . 2019 Mar;46(3-4):551-563. doi: 10.1007/s10295-018-02129-3.
Polytheonamides are the most extensively modified ribosomally synthesized and post-translationally modified peptide natural products (RiPPs) currently known. In RiPP biosynthesis, the processed peptide is usually released from a larger precursor by proteolytic cleavage to generate the bioactive terminal product of the pathway. For polytheonamides, which are members of a new RiPP family termed proteusins, we have recently shown that such cleavage is catalyzed by the cysteine protease PoyH acting on the precursor PoyA, both encoded in the polytheonamide biosynthetic gene cluster. We now report activity for PoyH under a variety of reaction conditions for different maturation states of PoyA and demonstrate a potential use of PoyH as a promiscuous protease to liberate and characterize RiPPs from other pathways. As a proof of concept, the identified recognition motif was introduced into precursors of the thiopeptide thiocillin and the lanthipeptide lichenicidin VK1, allowing for their site-specific cleavage with PoyH. Additionally, we show that PoyH cleavage is inhibited by PoyG, a previously uncharacterized chagasin-like protease inhibitor encoded in the polytheonamide gene cluster.
3. Thirteen posttranslational modifications convert a 14-residue peptide into the antibiotic thiocillin
Jon Clardy, Laura C Wieland Brown, Michael A Fischbach, Christopher T Walsh, Michael G Acker Proc Natl Acad Sci U S A . 2009 Feb 24;106(8):2549-53. doi: 10.1073/pnas.0900008106.
The thiazolylpeptides are a family of >50 bactericidal antibiotics that block the initial steps of bacterial protein synthesis. Here, we report a biosynthetic gene cluster for thiocillin and establish that it, and by extension the whole class, is ribosomally synthesized. Remarkably, the C-terminal 14 residues of a 52-residue peptide precursor undergo 13 posttranslational modifications to give rise to thiocillin, making this antibiotic the most heavily posttranslationally-modified peptide known to date.
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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 ╳
