Pacidamycin 1
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| Category | Bioactive by-products |
| Catalog number | BBF-02333 |
| CAS | 121264-05-9 |
| Molecular Weight | 874.90 |
| Molecular Formula | C41H50N10O12 |
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Description
It is produced by the strain of Str. coeruleorubidus AB 1183F-64. It has inhibitory effect on Pseudomonas aeruginosa. It also has effect on a few strains of bacteria such as suppurative staphylococcus and Escherichia coli. Serum can reduce its antibacterial activity, pH also affects its antibacterial activity. pH 6.5, The antibacterial activity of Pacidamycin 1 can be enhanced twice. In vivo test of mice infected with pseudomonas aeruginosa (100 mg/kg·d) showed no protective effect.
Specification
| Synonyms | Butanamide, N-[[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]carbonyl]-L-alanyl-N3-(L-alanyl-3-hydroxy-L-phenylalanyl)-2-amino-N-[(Z)-[(4R,5R)-5-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)dihydro-4-hydroxy-2(3H)-furanylidene]methyl]-3-(methylamino)-, (2S,3S)- |
| IUPAC Name | (2S)-2-[[(2S)-1-[[(2S,3S)-3-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(3-hydroxyphenyl)propanoyl]-methylamino]-1-[[(Z)-[(4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]carbamoylamino]-3-(1H-indol-3-yl)propanoic acid |
| Canonical SMILES | CC(C(C(=O)NC=C1CC(C(O1)N2C=CC(=O)NC2=O)O)NC(=O)C(C)NC(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O)N(C)C(=O)C(CC5=CC(=CC=C5)O)NC(=O)C(C)N |
| InChI | InChI=1S/C41H50N10O12/c1-20(42)34(55)46-29(15-23-8-7-9-25(52)14-23)37(58)50(4)22(3)33(36(57)44-19-26-17-31(53)38(63-26)51-13-12-32(54)48-41(51)62)49-35(56)21(2)45-40(61)47-30(39(59)60)16-24-18-43-28-11-6-5-10-27(24)28/h5-14,18-22,29-31,33,38,43,52-53H,15-17,42H2,1-4H3,(H,44,57)(H,46,55)(H,49,56)(H,59,60)(H2,45,47,61)(H,48,54,62)/b26-19-/t20-,21-,22-,29-,30-,31+,33-,38+/m0/s1 |
| InChI Key | PCVKUJRMSUSDPH-DLJJVGNLSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.493 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Total synthesis of pacidamycin D by Cu(I)-catalyzed oxy enamide formation
Kazuya Okamoto, Masahiro Sakagami, Fei Feng, Hiroko Togame, Hiroshi Takemoto, Satoshi Ichikawa, Akira Matsuda Org Lett. 2011 Oct 7;13(19):5240-3. doi: 10.1021/ol202124b. Epub 2011 Sep 8.
The first total synthesis of pacidamycin D, which is expected to be a good candidate as an antibacterial agent against P. aeruginosa, is described. The key elements of our approach feature an efficient and stereocontrolled construction of the Z-oxyvinyl iodide and copper-catalyzed cross-coupling with the tetrapeptide carboxamide.
2. Mechanism of action of the uridyl peptide antibiotics: an unexpected link to a protein-protein interaction site in translocase MraY
Maria T Rodolis, Agnes Mihalyi, Christian Ducho, Kornelia Eitel, Bertolt Gust, Rebecca J M Goss, Timothy D H Bugg Chem Commun (Camb). 2014 Nov 7;50(86):13023-5. doi: 10.1039/c4cc06516f.
The pacidamycin and muraymycin uridyl peptide antibiotics show some structural resemblance to an Arg-Trp-x-x-Trp sequence motif for protein-protein interaction between bacteriophage ϕX174 protein E and E. coli translocase MraY. Members of the UPA class, and a synthetic uridine-peptide analogue, were found to show reduced levels of inhibition to F288L or E287A mutant MraY enzymes, implying that the UPAs interact at this extracellular site as part of the enzyme inhibition mechanism.
3. Recent advances in the biosynthesis of nucleoside antibiotics
Taro Shiraishi, Tomohisa Kuzuyama J Antibiot (Tokyo). 2019 Dec;72(12):913-923. doi: 10.1038/s41429-019-0236-2. Epub 2019 Sep 25.
Nucleoside antibiotics are a diverse class of natural products with promising biomedical activities. These compounds contain a saccharide core and a nucleobase. Despite the large number of nucleoside antibiotics that have been reported, biosynthetic studies on these compounds have been limited compared with those on other types of natural products such as polyketides, peptides, and terpenoids. Due to recent advances in genome sequencing technology, the biosynthesis of nucleoside antibiotics has rapidly been clarified. This review covering 2009-2019 focuses on recent advances in the biosynthesis of nucleoside antibiotics.
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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 ╳
