Pacidamycin D
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02337 |
| CAS | 287107-95-3 |
| Molecular Weight | 711.72 |
| Molecular Formula | C32H41N9O10 |
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Description
It is produced by the strain of Streptomyces coeruleorubidus NRRL 18370. It's a Pacidamycin antibiotic. It has the activity against pseudomonas aeruginosa with MIC of 4-16 μg/mL. it has no effect on other gram-negative bacteria and gram-positive bacteria, and no effect on drug-resistant pseudomonas aeruginosa.
Specification
| IUPAC Name | (2S)-2-[[(2S)-1-[[(2S,3S)-3-[[(2S)-2-aminopropanoyl]-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(C)N |
| InChI | InChI=1S/C32H41N9O10/c1-15(33)28(46)40(4)17(3)25(27(45)35-14-19-12-23(42)29(51-19)41-10-9-24(43)38-32(41)50)39-26(44)16(2)36-31(49)37-22(30(47)48)11-18-13-34-21-8-6-5-7-20(18)21/h5-10,13-17,22-23,25,29,34,42H,11-12,33H2,1-4H3,(H,35,45)(H,39,44)(H,47,48)(H2,36,37,49)(H,38,43,50)/b19-14-/t15-,16-,17-,22-,23+,25-,29+/m0/s1 |
| InChI Key | PBFVZISIBPPZNE-SYZWNRCCSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-negative bacteria |
Reference Reading
1. A Pressure Test to Make 10 Molecules in 90 Days: External Evaluation of Methods to Engineer Biology
Arturo Casini, Fang-Yuan Chang, Raissa Eluere, Andrew M King, et al. J Am Chem Soc. 2018 Mar 28;140(12):4302-4316. doi: 10.1021/jacs.7b13292. Epub 2018 Mar 16.
Centralized facilities for genetic engineering, or "biofoundries", offer the potential to design organisms to address emerging needs in medicine, agriculture, industry, and defense. The field has seen rapid advances in technology, but it is difficult to gauge current capabilities or identify gaps across projects. To this end, our foundry was assessed via a timed "pressure test", in which 3 months were given to build organisms to produce 10 molecules unknown to us in advance. By applying a diversity of new approaches, we produced the desired molecule or a closely related one for six out of 10 targets during the performance period and made advances toward production of the others as well. Specifically, we increased the titers of 1-hexadecanol, pyrrolnitrin, and pacidamycin D, found novel routes to the enediyne warhead underlying powerful antimicrobials, established a cell-free system for monoterpene production, produced an intermediate toward vincristine biosynthesis, and encoded 7802 individually retrievable pathways to 540 bisindoles in a DNA pool. Pathways to tetrahydrofuran and barbamide were designed and constructed, but toxicity or analytical tools inhibited further progress. In sum, we constructed 1.2 Mb DNA, built 215 strains spanning five species ( Saccharomyces cerevisiae, Escherichia coli, Streptomyces albidoflavus, Streptomyces coelicolor, and Streptomyces albovinaceus), established two cell-free systems, and performed 690 assays developed in-house for the molecules.
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. Cu-mediated enamide formation in the total synthesis of complex peptide natural products
Takefumi Kuranaga, Yusuke Sesoko, Masayuki Inoue Nat Prod Rep. 2014 Apr;31(4):514-32. doi: 10.1039/c3np70103d. Epub 2014 Feb 25.
Cu-mediated C(sp(2))-N bond formation has received intense interest recently, and has been applied to the total synthesis of a wide variety of structurally complex natural products. This review covers the synthetic assembly of peptide natural products in which Cu-mediated enamide formation is the key transformation. The total syntheses of cyclopeptide alkaloids, pacidamycin D, and yaku'amide A exemplify the versatility of the Cu-catalyzed cross-coupling reaction in comparison to other synthetic methods.
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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 ╳
