Albomycin δ1
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| Category | Antibiotics |
| Catalog number | BBF-00408 |
| CAS | 1414-39-7 |
| Molecular Weight | 1006.81 |
| Molecular Formula | C36H58FeN10O18S3+ |
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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(1); CHEBI:83206; [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)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrothiophen-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)-3,4-dihydroxy-5-(3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrothiophen-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)-3,4-dihydroxy-5-(3-methyl-2,4-dioxopyrimidin-1-yl)thiolan-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(=O)N(C2=O)C)O)O)O)C(=O)O)N)O.[Fe] |
| InChI | InChI=1S/C36H58N10O18S.Fe/c1-17(48)44(62)12-5-8-20(37)30(55)38-21(9-6-13-45(63)18(2)49)31(56)39-22(10-7-14-46(64)19(3)50)32(57)40-23(16-47)33(58)41-25(35(59)60)26(52)29-27(53)28(54)34(65-29)43-15-11-24(51)42(4)36(43)61;/h11,15,20-23,25-29,34,47,52-54,62-64H,5-10,12-14,16,37H2,1-4H3,(H,38,55)(H,39,56)(H,40,57)(H,41,58)(H,59,60);/t20-,21-,22-,23-,25+,26-,27+,28+,29+,34+;/m0./s1 |
| InChI Key | JIWVRUCWILWDHP-DFBZBFILSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. 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.
2. Synthesis and structural insights into the binding mode of the albomycin δ1 core and its analogues in complex with their target aminoacyl-tRNA synthetase
Bharat Gadakh, Gaston Vondenhoff, Luping Pang, Manesh Nautiyal, Steff De Graef, Sergei V Strelkov, Stephen D Weeks, Arthur Van Aerschot Bioorg Med Chem. 2020 Sep 1;28(17):115645. doi: 10.1016/j.bmc.2020.115645. Epub 2020 Jul 13.
Despite of proven efficacy and well tolerability, albomycin is not used clinically due to scarcity of material. Several attempts have been made to increase the production of albomycin by chemical or biochemical methods. In the current study, we have synthesized the active moiety of albomycin δ1 and investigated its binding mode to its molecular target seryl-trna synthetase (SerRS). In addition, isoleucyl and aspartyl congeners were prepared to investigate whether the albomycin scaffold can be extrapolated to target other aminoacyl-tRNA synthetases (aaRSs) from both class I and class II aaRSs, respectively. The synthesized analogues were evaluated for their ability to inhibit the corresponding aaRSs by an in vitro aminoacylation experiment using purified enzymes. It was observed that the diastereomer having the 5'S, 6'R-configuration (nucleoside numbering) as observed in the crystal structure, exhibits excellent inhibitory activity in contrast to poor activity of its companion 5'R,6'S-diasteromer obtained as byproduct during synthesis. Moreover, the albomycin core scaffold seems well tolerated for class II aaRSs inhibition compared with class I aaRSs. To understand this bias, we studied X-ray crystal structures of SerRS in complex with the albomycin δ1 core structure 14a, and AspRS in complex with compound 16a. Structural analysis clearly showed that diastereomer selectivity is attributed to the steric restraints of the active site of SerRS and AspRS.
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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 ╳
