Albomycin δ2
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| Category | Antibiotics |
| Catalog number | BBF-00409 |
| CAS | |
| Molecular Weight | 1048.85 |
| Molecular Formula | C37H60FeN12O18S3+ |
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Description
It is produced by the strain of Streptomyces subtropicus. It has anti-gram-positive and negative bacterial activities. The iron was removed with hydroxyquinoline, and the antibacterial activity disappeared. The FeCl3 solution was added to restore the activity completely.
Specification
| Synonyms | albomycin delta(2); CHEBI:83215; [N(5)-acetyl-N(5)-(hydroxy-kappaO)-L-ornithyl-N(5)-acetyl-N(5)-(hydroxy-kappaO)-L-ornithyl-N(5)-acetyl-N(5)-(hydroxy-kappaO)-L-ornithyl-L-seryl-(3S)-3-{(2R,3R,4R,5R)-5-[4-(carbamoylimino)-3-methyl-2-oxo-3,4-dihydropyrimidin-1(2H)-yl]-3,4-dihydroxytetrahydrothiophen-2-yl}-D-serinato(3-)]iron; iron(3+) N(5)-acetyl-N(5)-oxido-L-ornithyl-N(5)-acetyl-N(5)-oxido-L-ornithyl-N(5)-acetyl-N(5)-oxido-L-ornithyl-L-seryl-(3S)-3-{(2R,3R,4R,5R)-5-[4-(carbamoylimino)-3-methyl-2-oxo-3,4-dihydropyrimidin-1(2H)-yl]-3,4-dihydroxytetrahydrothiophen-2-yl}-D-serine |
| IUPAC Name | (2R,3S)-2-[[(2S)-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-[[(2S)-5-[acetyl(hydroxy)amino]-2-aminopentanoyl]amino]pentanoyl]amino]pentanoyl]amino]-3-hydroxypropanoyl]amino]-3-[(2R,3R,4R,5R)-5-[(4E)-4-carbamoylimino-3-methyl-2-oxopyrimidin-1-yl]-3,4-dihydroxythiolan-2-yl]-3-hydroxypropanoic acid;iron |
| Canonical SMILES | CC(=O)N(CCCC(C(=O)NC(CCCN(C(=O)C)O)C(=O)NC(CCCN(C(=O)C)O)C(=O)NC(CO)C(=O)NC(C(C1C(C(C(S1)N2C=CC(=NC(=O)N)N(C2=O)C)O)O)O)C(=O)O)N)O.[Fe] |
| InChI | InChI=1S/C37H60N12O18S.Fe/c1-17(51)47(65)12-5-8-20(38)30(57)40-21(9-6-13-48(66)18(2)52)31(58)41-22(10-7-14-49(67)19(3)53)32(59)42-23(16-50)33(60)44-25(35(61)62)26(54)29-27(55)28(56)34(68-29)46-15-11-24(43-36(39)63)45(4)37(46)64;/h11,15,20-23,25-29,34,50,54-56,65-67H,5-10,12-14,16,38H2,1-4H3,(H2,39,63)(H,40,57)(H,41,58)(H,42,59)(H,44,60)(H,61,62);/b43-24+;/t20-,21-,22-,23-,25+,26-,27+,28+,29+,34+;/m0./s1 |
| InChI Key | XEGJEKIQLBLKHJ-IDJYBIRTSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Identification of the Enzymes Mediating the Maturation of the Seryl-tRNA Synthetase Inhibitor SB-217452 during the Biosynthesis of Albomycins
Richiro Ushimaru, Zhang Chen, Houyuan Zhao, Po-Hsun Fan, Hung-Wen Liu Angew Chem Int Ed Engl. 2020 Feb 24;59(9):3558-3562. doi: 10.1002/anie.201915275. Epub 2020 Jan 29.
Albomycin δ2 is a sulfur-containing sideromycin natural product that shows potent antibacterial activity against clinically important pathogens. The l-serine-thioheptose dipeptide partial structure, known as SB-217452, has been found to be the active seryl-tRNA synthetase inhibitor component of albomycin δ2 . Herein, it is demonstrated that AbmF catalyzes condensation between the 6'-amino-4'-thionucleoside with the d-ribo configuration and seryl-adenylate supplied by the serine adenylation activity of AbmK. Formation of the dipeptide is followed by C3'-epimerization to produce SB-217452 with the d-xylo configuration, which is catalyzed by the radical S-adenosyl-l-methionine enzyme AbmJ. Gene deletion suggests that AbmC is involved in peptide assembly linking SB-217452 with the siderophore moiety. This study establishes how the albomycin biosynthetic machinery generates its antimicrobial component SB-217452.
2. Total synthesis and antimicrobial evaluation of natural albomycins against clinical pathogens
Zihua Lin, Xiaobo Xu, Sheng Zhao, Xiaohong Yang, Jian Guo, Qun Zhang, Chunmei Jing, Shawn Chen, Yun He Nat Commun. 2018 Sep 4;9(1):3445. doi: 10.1038/s41467-018-05821-1.
Development of effective antimicrobial agents continues to be a great challenge, particularly due to the increasing resistance of superbugs and frequent hospital breakouts. There is an urgent need for more potent and safer antibiotics with novel scaffolds. As historically many commercial drugs were derived from natural products, discovery of antimicrobial agents from complex natural product structures still holds a great promise. Herein, we report the total synthesis of natural albomycins δ1 (1a), δ2 (1b), and ε (1c), which validates the structures of these peptidylnucleoside compounds and allows for synthetic access to bioactive albomycin analogs. The efficient synthesis of albomycins enables extensive evaluations of these natural products against model bacteria and clinical pathogens. Albomycin δ2 has the potential to be developed into an antibacterial drug to treat Streptococcus pneumoniae and Staphylococcus aureus infections.
3. A New Albomycin-Producing Strain of Streptomyces globisporus subsp. globisporus May Provide Protection for Ants Messor structor
Yuliya V Zakalyukina, Nikolay A Pavlov, Dmitrii A Lukianov, Valeria I Marina, Olga A Belozerova, Vadim N Tashlitsky, Elena B Guglya, Ilya A Osterman, Mikhail V Biryukov Insects. 2022 Nov 11;13(11):1042. doi: 10.3390/insects13111042.
There are several well-studied examples of protective symbiosis between insect host and symbiotic actinobacteria, producing antimicrobial metabolites to inhibit host pathogens. These mutualistic relationships are best described for some wasps and leaf-cutting ants, while a huge variety of insect species still remain poorly explored. For the first time, we isolated actinobacteria from the harvester ant Messor structor and evaluated the isolates' potential as antimicrobial producers. All isolates could be divided into two morphotypes of single and mycelial cells. We found that the most common mycelial morphotype was observed among soldiers and least common among larvae in the studied laboratory colony. The representative of this morphotype was identified as Streptomyces globisporus subsp. globisporus 4-3 by a polyphasic approach. It was established using a E. coli JW5503 pDualRep2 system that crude broths of mycelial isolates inhibited protein synthesis in reporter strains, but it did not disrupt the in vitro synthesis of proteins in cell-free extracts. An active compound was extracted, purified and identified as albomycin δ2. The pronounced ability of albomycin to inhibit the growth of entomopathogens suggests that Streptomyces globisporus subsp. globisporus may be involved in defensive symbiosis with the Messor structor ant against infections.
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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 ╳
