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pyoverdine
Sign in to savePyoverdines (alternatively, and less commonly, spelled as pyoverdins) are fluorescent siderophores produced by certain pseudomonads. Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient (i.e., iron), regulation of other virulence factors (including exotoxin A and the protease PrpL), supporting the formation of biofilms, and are increasingly recognized for having toxicity themselves.
Chemical data
- Formula
- C56H88N18O22
- Molecular weight
- 1365.4 g/mol
- IUPAC name
- 2-amino-5-[[(1S)-1-[[1-[[5-(diaminomethylideneamino)-1-[[1-[[5-[formyl(hydroxy)amino]-1-[[9-[3-[formyl(hydroxy)amino]propyl]-3,6-bis(1-hydroxyethyl)-2,5,8,11-tetraoxo-1,4,7,10-tetrazacyclohexadec-12-yl]amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamoyl]-8,9-dihydroxy-2,3,4,4a-tetrahydro-1H-pyrimido[1,2-a]quinolin-5-yl]amino]-5-oxopentanoic acid
- SMILES
- CC(C1C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN(C=O)O)NC(=O)C(CCCN(C=O)O)NC(=O)C(CO)NC(=O)C(CCCN=C(N)N)NC(=O)C(CO)NC(=O)[C@@H]2CCNC3N2C4=CC(=C(C=C4C=C3NC(=O)CCC(C(=O)O)N)O)O)C(C)O)O
- InChIKey
- QIRRYPHVUMPBDX-UARRTFJPSA-N
- XLogP
- -9.7
- Polar surface area
- 636 Ų
- H-bond donors
- 23
- H-bond acceptors
- 26
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- siderophore
Show 1 more fact
- SMARTS notation
- [#7][#6]1~[#6]~[#6]2~[#6]~[#6]~[#6]~[#6]~[#6]~2~[#7]2~[#6]~1~[#7]~[#6]~[#6]~[#6]~2C(~O)~N
Sources (2)
via Wikidata · CC0
~17 min read
Encyclopedic overview
18 sectionsContents
- Biological functions
- Structure and characteristics
- Structure
- Characteristics
- Synthesis
- Biosynthesis
- Core
- Peptide chain
- Ketoacid
- Maturation and export
- Total chemical synthesis
- Mechanisms of virulence
- Role in microbial cooperation
- Nomenclature
- History
- Other uses
- Pseudoverdine
- References
Pyoverdines (alternatively, and less commonly, spelled as pyoverdins) are fluorescent siderophores produced by certain pseudomonads. Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient (i.e., iron), regulation of other virulence factors (including exotoxin A and the protease PrpL), supporting the formation of biofilms, and are increasingly recognized for having toxicity themselves.
Pyoverdines have also been investigated as "Trojan Horse" molecules for the delivery of antimicrobials to otherwise resistant bacterial strains, as chelators that can be used for bioremediation of heavy metals, and as fluorescent reporters used to assay for the presence of iron and potentially other metals.
Excerpted from Wikipedia’s “pyoverdine” article, available under the CC BY-SA 4.0 licence.
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