Polyoxin N
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02046 |
| CAS | 37362-29-1 |
| Molecular Weight | 477.38 |
| Molecular Formula | C16H23N5O12 |
Online Inquiry
Description
Polyoxin is a nucleoside antifungal antibiotic produced by Str. cacaor var. asoensis and Str. piomogenus.
Specification
| Synonyms | Allofuranuronic acid, 5-((2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonamino)-1,5-dideoxy-1-(4-formyl-2,3-dihydro-2-oxo-1H-imidazol-1-yl)-, beta-D- |
| IUPAC Name | 2-[(2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl)amino]-2-[5-(5-formyl-2-oxo-1H-imidazol-3-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid |
| Canonical SMILES | C1=C(NC(=O)N1C2C(C(C(O2)C(C(=O)O)NC(=O)C(C(C(COC(=O)N)O)O)N)O)O)C=O |
| InChI | InChI=1S/C16H23N5O12/c17-6(8(24)5(23)3-32-15(18)30)12(27)20-7(14(28)29)11-9(25)10(26)13(33-11)21-1-4(2-22)19-16(21)31/h1-2,5-11,13,23-26H,3,17H2,(H2,18,30)(H,19,31)(H,20,27)(H,28,29) |
| InChI Key | OSWKWKBETDCHCA-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 190°C (dec.) |
| Density | 1.8±0.1 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. An ATP-Dependent Ligase with Substrate Flexibility Involved in Assembly of the Peptidyl Nucleoside Antibiotic Polyoxin
Rong Gong, Jianzhao Qi, Pan Wu, You-Sheng Cai, Hongmin Ma, Yang Liu, He Duan, Meng Wang, Zixin Deng, Neil P J Price, Wenqing Chen Appl Environ Microbiol. 2018 Jun 18;84(13):e00501-18. doi: 10.1128/AEM.00501-18. Print 2018 Jul 1.
Polyoxin (POL) is an unusual peptidyl nucleoside antibiotic, in which the peptidyl moiety and nucleoside skeleton are linked by an amide bond. However, their biosynthesis remains poorly understood. Here, we report the deciphering of PolG as an ATP-dependent ligase responsible for the assembly of POL. A polG mutant is capable of accumulating multiple intermediates, including the peptidyl moiety (carbamoylpolyoxamic acid [CPOAA]) and the nucleoside skeletons (POL-C and the previously overlooked thymine POL-C). We further demonstrate that PolG employs an ATP-dependent mechanism for amide bond formation and that the generation of the hybrid nucleoside antibiotic POL-N is also governed by PolG. Finally, we determined that the deduced ATP-binding sites are functionally essential for PolG and that they are highly conserved in a number of related ATP-dependent ligases. These insights have allowed us to propose a catalytic mechanism for the assembly of peptidyl nucleoside antibiotic via an acyl-phosphate intermediate and have opened the way for the combinatorial biosynthesis/pathway engineering of this group of nucleoside antibiotics.IMPORTANCE POL is well known for its remarkable antifungal bioactivities and unusual structural features. Actually, elucidation of the POL assembly logic not only provides the enzymatic basis for further biosynthetic understanding of related peptidyl nucleoside antibiotics but also contributes to the rational generation of more hybrid nucleoside antibiotics via synthetic biology strategy.
2. Novel polyoxins generated by heterologously expressing polyoxin biosynthetic gene cluster in the sanN inactivated mutant of Streptomyces ansochromogenes
Jine Li, Lei Li, Chi Feng, Yihua Chen, Huarong Tan Microb Cell Fact. 2012 Oct 8;11:135. doi: 10.1186/1475-2859-11-135.
Background: Polyoxins are potent inhibitors of chitin synthetases in fungi and insects. The gene cluster responsible for biosynthesis of polyoxins has been cloned and sequenced from Streptomyces cacaoi and tens of polyoxin analogs have been identified already. Results: The polyoxin biosynthetic gene cluster from Streptomyces cacaoi was heterologously expressed in the sanN inactivated mutant of Streptomyces ansochromogenes as a nikkomycin producer. Besides hybrid antibiotics (polynik A and polyoxin N) and some known polyoxins, two novel polyoxin analogs were accumulated. One of them is polyoxin P that has 5-aminohexuronic acid with N-glycosidically bound thymine as the nucleoside moiety and dehydroxyl-carbamoylpolyoxic acid as the peptidyl moiety. The other analog is polyoxin O that contains 5-aminohexuronic acid bound thymine as the nucleoside moiety, but recruits polyoximic acid as the sole peptidyl moiety. Bioassay against phytopathogenic fungi showed that polyoxin P displayed comparatively strong inhibitory activity, whereas the inhibitory activity of polyoxin O was weak under the same testing conditions. Conclusion: Two novel polyoxin analogs (polyoxin P and O) were generated by the heterologous expression of polyoxin biosynthetic gene cluster in the sanN inactivated mutant of Streptomyces ansochromogenes. Polyoxin P showed potent antifungal activity,while the activity of polyoxin O was weak. The strategy presented here may be available for other antibiotics producers.
3. Genetic dissection of the polyoxin building block-carbamoylpolyoxamic acid biosynthesis revealing the "pathway redundancy" in metabolic networks
Wenqing Chen, Daofeng Dai, Changchun Wang, Tingting Huang, Lipeng Zhai, Zixin Deng Microb Cell Fact. 2013 Dec 7;12:121. doi: 10.1186/1475-2859-12-121.
Background: Polyoxin, a peptidyl nucleoside antibiotic, consists of three building blocks including a nucleoside skeleton, polyoximic acid (POIA), and carbamoylpolyoxamic acid (CPOAA), however, little is known about the "pathway redundancy" of the metabolic networks directing the CPOAA biosynthesis in the cell factories of the polyoxin producer. Results: Here we report the genetic characterization of CPOAA biosynthesis with revealing a "pathway redundancy" in metabolic networks. Independent mutation of the four genes (polL-N and polP) directly resulted in the accumulation of polyoxin I, suggesting their positive roles for CPOAA biosynthesis. Moreover, the individual mutant of polN and polP also partially retains polyoxin production, suggesting the existence of the alternative homologs substituting their functional roles. Conclusions: It is unveiled that argA and argB in L-arginine biosynthetic pathway contributed to the "pathway redundancy", more interestingly, argB in S. cacaoi is indispensible for both polyoxin production and L-arginine biosynthesis. These data should provide an example for the research on the "pathway redundancy" in metabolic networks, and lay a solid foundation for targeted enhancement of polyoxin production with synthetic biology strategies.
Recommended Products
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
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 ╳
