Ezomycin A2
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00895 |
| CAS | 54328-22-2 |
| Molecular Weight | 530.44 |
| Molecular Formula | C19H26N6O12 |
Online Inquiry
Description
Ezomycin A2 is an antifungal antibiotic produced by Streptomyces kitazawaensis 009. It is mainly active against phytopathogens such as Sclerotinia sclerotiorum and Botrytis, and has a control effect on sclerotinia, botrytis and candidiasis of crops.
Specification
| IUPAC Name | (2R,3R,3aS,5S,6R,7S,7aR)-6-[(2R,3R,4R,6S)-4-amino-6-carboxy-3-hydroxyoxan-2-yl]oxy-2-(4-amino-2-oxopyrimidin-1-yl)-7-(carbamoylamino)-3-hydroxy-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-5-carboxylic acid |
| Canonical SMILES | C1C(C(C(OC1C(=O)O)OC2C(C3C(C(C(O3)N4C=CC(=NC4=O)N)O)OC2C(=O)O)NC(=O)N)O)N |
| InChI | InChI=1S/C19H26N6O12/c20-4-3-5(15(28)29)34-17(8(4)26)37-11-7(24-18(22)32)10-12(35-13(11)16(30)31)9(27)14(36-10)25-2-1-6(21)23-19(25)33/h1-2,4-5,7-14,17,26-27H,3,20H2,(H,28,29)(H,30,31)(H2,21,23,33)(H3,22,24,32)/t4-,5+,7+,8-,9-,10-,11-,12+,13+,14-,17+/m1/s1 |
| InChI Key | VYWQXSLVJADWLT-VWBNVUAGSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 200°C(dec.) |
Reference Reading
1. Construction of an octosyl acid backbone catalyzed by a radical S-adenosylmethionine enzyme and a phosphatase in the biosynthesis of high-carbon sugar nucleoside antibiotics
Nisha He, Pan Wu, Yongxing Lei, Baofu Xu, Xiaochen Zhu, Gudan Xu, Yaojie Gao, Jianzhao Qi, Zixin Deng, Gongli Tang, Wenqing Chen, Youli Xiao Chem Sci. 2017 Jan 1;8(1):444-451. doi: 10.1039/c6sc01826b. Epub 2016 Aug 19.
Unique bicyclic octosyl uronic acid nucleosides include ezomycin, malayamycin, and octosyl acid (OA). They are structurally characterized by OA, an unusual 8-carbon furanosyl nucleoside core proposed to be the precursor to polyoxin and nikkomycin. Despite the well-known bioactivity of these nucleoside antibiotics, the biosynthesis of OA has not been elucidated yet. Here we report the two pivotal enzymatic steps in the polyoxin biosynthetic pathway leading to the identification of OA as a key intermediate. Our data suggest that this intermediate is formed via a free radical reaction catalyzed by the radical S-adenosylmethionine (SAM) enzyme, PolH, and using 3'-enolpyruvyl uridine 5'-monophosphate (3'-EUMP) as a substrate. Subsequent dephosphorylation catalyzed by phosphatase PolJ converts the resulting octosyl acid 5'-phosphate (OAP) to OA. These results provide, for the first time, significant in vitro evidence for the biosynthetic origins of the C8 backbone of OA.
2. Synthetic studies on ezomycins: stereoselective route to a thymine octosyl nucleoside derivative
Juhienah K Khalaf, David G VanderVelde, Apurba Datta J Org Chem. 2008 Aug 1;73(15):5977-84. doi: 10.1021/jo801050r. Epub 2008 Jul 4.
The ezomycins are Streptomyces-derived antifungal natural products, belonging to the complex peptidyl nucleoside family of antibiotics. Employing D-serine as a chiral platform, we report herein a novel synthetic route to the bicyclic octosyl nucleoside core of the ezomycins. A key step in the sequence involved a stereoselective 6-exo-trig oxymercurationoxidation of a strategic delta-hydroxy alkene derivative, toward construction of the trans-fused furopyran ring system as present in the target products. In contrast to the known carbohydrate-based synthetic routes to the above furopyranyl fragment, the present amino acid chiral template approach is expected to offer a more flexible pathway toward potential SAR-targeted structural/stereochemical modifications of this central bicyclic nucleoside component of the ezomycins.
3. Stereoselective route to the ezoaminuroic acid core of the ezomycins
Juhienah K Khalaf, Apurba Datta J Org Chem. 2005 Aug 19;70(17):6937-40. doi: 10.1021/jo051086n.
Starting from readily available (R)-glycidol, an efficient pathway to a strategically functionalized ezoaminuroic acid derivative of the antifungal ezomycins has been developed. A key transformation in the synthesis involves regio- and stereoselective conversion of the olefinic functionality of a 5,6-dihydropyran-2-one to the C-2, C-3 trans-1,2-amino alcohol moiety as present in ezoaminuroic acid.
Recommended Products
| BBF-01825 | Loganin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | 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 ╳
