Pseudouridimycin
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| Category | Antibiotics |
| Catalog number | BBF-05723 |
| CAS | 1566586-52-4 |
| Molecular Weight | 486.44 |
| Molecular Formula | C17H26N8O9 |
| Purity | ≥95% |
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Description
Pseudouridimycin is a C-nucleoside analogue that selectively inhibits bacterial RNA polymerase. Pseudouridimycin is an antibiotic found in Streptomyces albus that has activity against Gram-positive and Gram-negative bacteria.
Specification
| Synonyms | PUM; 2,4(1H,3H)-Pyrimidinedione, 5-(5-((N-(aminoiminomethyl)glycyl-N2-hydroxy-L-glutaminyl)amino)-5-deoxy-beta-D-ribofuranosyl)-; (1S)-1,4-Anhydro-5-[(N-carbamimidoylglycyl-N2-hydroxy-L-glutaminyl)amino]-5-deoxy-1-(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)-D-ribitol; D-Ribitol, 5-[[N-(aminoiminomethyl)glycyl-N2-hydroxy-L-glutaminyl]amino]-1,4-anhydro-5-deoxy-1-C-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidinyl)-, (1S)- |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-[[2-(diaminomethylideneamino)acetyl]-hydroxyamino]-N-[[(2R,3S,4R,5S)-5-(2,4-dioxo-1H-pyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methyl]pentanediamide |
| Canonical SMILES | C1=C(C(=O)NC(=O)N1)C2C(C(C(O2)CNC(=O)C(CCC(=O)N)N(C(=O)CN=C(N)N)O)O)O |
| InChI | InChI=1S/C17H26N8O9/c18-9(26)2-1-7(25(33)10(27)5-22-16(19)20)15(31)21-4-8-11(28)12(29)13(34-8)6-3-23-17(32)24-14(6)30/h3,7-8,11-13,28-29,33H,1-2,4-5H2,(H2,18,26)(H,21,31)(H4,19,20,22)(H2,23,24,30,32)/t7-,8+,11+,12+,13-/m0/s1 |
| InChI Key | XDEYHXABZOKKDZ-YFKLLHAASA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.91±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO |
Reference Reading
1. Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction
Satoshi Ichikawa, Courtney C Aldrich, Ryotaro Okawa Chem Commun (Camb) . 2022 Jul 14;58(57):7956-7959. doi: 10.1039/d2cc02442j.
A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessibleviaa longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.
2. Heterologous Expression of Pseudouridimycin and Description of the Corresponding Minimal Biosynthetic Gene Cluster
Maria A Patras, Till F Schäberle, Nils Böhringer Molecules . 2021 Jan 19;26(2):510. doi: 10.3390/molecules26020510.
Pseudouridimycin (PUM) was recently discovered fromStreptomycessp. DSM26212 as a novel bacterial nucleoside analog that competes with UTP for access to the RNA polymerase (RNAP) active site, thereby inhibiting bacterial RNAP by blocking transcription. This represents a novel antibacterial mode of action and it is known that PUM inhibits bacterial RNAP in vitro, inhibits bacterial growth in vitro, and was active in vivo in a mouse infection model ofStreptococcus pyogenesperitonitis. The biosynthetic gene cluster (BGC) was previously identified and characterized by knockout experiments. However, the minimal set of genes necessary for PUM production was not proposed. To identify the minimal BGC and to create a plug-and-play production platform for PUM and its biosynthetic precursors, several versions of a redesigned PUM BGC were generated and expressed in the heterologous hostStreptomyces coelicolorM1146 under control of strong promotors. Heterologous expression allowed identification of the putative serine/threonine kinase PumF as an enzyme essential for heterologous PUM production and thus corroboration of the PUM minimal BGC.
3. Blocks in the pseudouridimycin pathway unlock hidden metabolites in the Streptomyces producer strain
Matteo Simone, Marianna Iorio, Richard H Ebright, Margherita Sosio, Sahar Davatgarbenam, Mitja M Zdouc, Stefania Serina, Stefano Donadio, Paolo Criscenzo, Sonia I Maffioli Sci Rep . 2021 Mar 12;11(1):5827. doi: 10.1038/s41598-021-84833-2.
We report a metabolomic analysis of Streptomyces sp. ID38640, a soil isolate that produces the bacterial RNA polymerase inhibitor pseudouridimycin. The analysis was performed on the wild type, on three newly constructed and seven previously reported mutant strains disabled in different genes required for pseudouridimycin biosynthesis. The results indicate that Streptomyces sp. ID38640 is able to produce, in addition to lydicamycins and deferroxiamines, as previously reported, also the lassopeptide ulleungdin, the non-ribosomal peptide antipain and the osmoprotectant ectoine. The corresponding biosynthetic gene clusters were readily identified in the strain genome. We also detected the known compound pyridindolol, for which we propose a previously unreported biosynthetic gene cluster, as well as three families of unknown metabolites. Remarkably, the levels of most metabolites varied strongly in the different mutant strains, an observation that enabled detection of metabolites unnoticed in the wild type. Systematic investigation of the accumulated metabolites in the ten different pum mutants identified shed further light on pseudouridimycin biosynthesis. We also show that several Streptomyces strains, able to produce pseudouridimycin, have distinct genetic relationship and metabolic profile with ID38640.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
