Polyoxin C
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| Category | Antibiotics |
| Catalog number | BBF-02045 |
| CAS | 21027-33-8 |
| Molecular Weight | 317.25 |
| Molecular Formula | C11H15N3O8 |
| Purity | >98% |
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Description
Polyoxin C is a nucleoside antifungal antibiotic produced by Str. cacaor var. asoensis and Str. piomogenus.
Specification
| Synonyms | Julimycin C |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid |
| Canonical SMILES | C1=C(C(=O)NC(=O)N1C2C(C(C(O2)C(C(=O)O)N)O)O)CO |
| InChI | InChI=1S/C11H15N3O8/c12-4(10(19)20)7-5(16)6(17)9(22-7)14-1-3(2-15)8(18)13-11(14)21/h1,4-7,9,15-17H,2,12H2,(H,19,20)(H,13,18,21)/t4-,5-,6+,7+,9+/m0/s1 |
| InChI Key | TZQKKPBFBDTCRN-AJDRIWCOSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 260-267°C (dec.) |
| Density | 1.8±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Application of the Ugi reaction for the one-pot synthesis of uracil polyoxin C analogues
Andrew Plant, Peter Thompson, David M Williams J Org Chem. 2009 Jul 3;74(13):4870-3. doi: 10.1021/jo900244m.
A simple, two-step synthesis of amide derivatives of uracil polyoxin C (UPOC) methyl ester using the Ugi reaction is described. The four components employed in the Ugi reaction are 2',3'-isopropylidine-protected uridine-5'-aldehyde, 2,4-dimethoxybenzylamine, an isoxazolecarboxylic acid, and the convertible isonitrile N-(2-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)carbonitrile. Following the Ugi reaction, treatment with HCl in MeOH achieves deprotection of the isopropylidene group and the N-benzyl group and conversion of the isonitrile-derived amide (the Ugi product) into the corresponding methyl ester. The procedure is amenable to automated multiparallel synthesis of novel compounds related to the polyoxin and nikkomycin nucleoside-peptide antibiotics.
2. Syntheses of carbocyclic uracil polyoxin C analogs: application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone
Cara Cesario, Marvin J Miller J Org Chem. 2009 Aug 7;74(15):5730-3. doi: 10.1021/jo900861x.
Carbocyclic uracil polyoxin C analogs are prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct in fewer than nine steps. Pd(0)/InI-mediated allylation of 4-acetoxy-2-azetidinone is used to install the beta-amino acid side chain at the C-5' position of the carbocycle.
3. Stereoselective synthesis of novel uracil polyoxin C conjugates as substrate analogues of chitin synthase
Andrew Plant, Peter Thompson, David M Williams J Org Chem. 2008 May 16;73(10):3714-24. doi: 10.1021/jo702564y. Epub 2008 Apr 24.
Stereoselective syntheses of both the natural (C5'- S) and unnatural (C5'- R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.
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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 ╳
