Albomycin epsilon

Albomycin epsilon

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Category Antibiotics
Catalog number BBF-00407
CAS 12676-10-7
Molecular Weight 1002.80
Molecular Formula C36H56FeN11O17S

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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 2FI7OQF5OS; Q27156693
IUPAC Name (2R,3S)-2-[[(2S)-2-[[(2S)-5-[acetyl(oxido)amino]-2-[[(2S)-5-[acetyl(oxido)amino]-2-[[(2S)-5-[acetyl(oxido)amino]-2-aminopentanoyl]amino]pentanoyl]amino]pentanoyl]amino]-3-hydroxypropanoyl]amino]-3-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(4-imino-3-methyl-2-oxopyrimidin-1-yl)thiolan-2-yl]-3-hydroxypropanoate;hydron;iron(3+)
Canonical SMILES [H+].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(=N)N(C2=O)C)O)O)O)C(=O)[O-])N)[O-].[Fe+3]
InChI InChI=1S/C36H56N11O17S.Fe/c1-17(49)45(62)12-5-8-20(37)30(55)39-21(9-6-13-46(63)18(2)50)31(56)40-22(10-7-14-47(64)19(3)51)32(57)41-23(16-48)33(58)42-25(35(59)60)26(52)29-27(53)28(54)34(65-29)44-15-11-24(38)43(4)36(44)61;/h11,15,20-23,25-29,34,38,48,52-54H,5-10,12-14,16,37H2,1-4H3,(H,39,55)(H,40,56)(H,41,57)(H,42,58)(H,59,60);/q-3;+3/t20-,21-,22-,23-,25+,26-,27+,28+,29+,34+;/m0./s1
InChI Key VQCJCCMAGPCDIK-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.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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