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Lenoremycin sodium

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Lenoremycin sodium
Category Antibiotics
Catalog number BBF-03029
CAS 58399-44-3
Molecular Weight 873.10
Molecular Formula C47H77NaO13

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is a polyether antibiotic produced by the strain of Streptomyces hygroscopicus A-130. It has the effect of anti-gram-positive bacteria, mycobacterium and protozoa, and can be used as a feed additive to control Eimeriatenella infection.

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Related CAS 51257-84-2 (free acid)
Synonyms Antibiotic A130 sodium salt; Dianemycin, 10-demethyl-19-de((tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy)-12-methyl-11-O-(tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)-, monosodium salt, (11(2R,5S,6R),12R)-; Antibiotic A-130A Sodium salt
IUPAC Name sodium;(E,2S,4R,8S)-8-[(2S,5R,6R,7R,9S)-2-[(2R,4S,6R,9R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-4,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-7-[(2R,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoate
Canonical SMILES CC1CCC(OC12C(CC(O2)C3C(CC(C(O3)(CO)O)C)C)C)C4(CCC5(O4)C(C(CC(O5)C(C)C=C(C)C(=O)C(C)CC(C)C(=O)[O-])OC6CCC(C(O6)C)OC)C)C.[Na+]
InChI InChI=1S/C47H78O13.Na/c1-25(19-26(2)41(49)27(3)20-29(5)43(50)51)36-23-37(55-40-16-14-35(53-12)34(10)54-40)33(9)46(56-36)18-17-44(11,60-46)39-15-13-30(6)47(58-39)32(8)22-38(57-47)42-28(4)21-31(7)45(52,24-48)59-42;/h19,25,27-40,42,48,52H,13-18,20-24H2,1-12H3,(H,50,51);/q;+1/p-1/b26-19+;/t25-,27+,28-,29-,30+,31+,32-,33+,34+,35-,36-,37+,38+,39+,40-,42-,44-,45-,46+,47?;/m0./s1
InChI Key SLTQRBSNSQCBNO-GZEIRFRYSA-M
Appearance Colorless Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Mycobacteria; Parasites
Melting Point 227-231°C
Solubility Soluble in Ethanol, Chloroform
1. Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6
Khaled A Shaaban, Meredith A Saunders, Yinan Zhang, Tuan Tran, Sherif I Elshahawi, Larissa V Ponomareva, Xiachang Wang, Jianjun Zhang, Gregory C Copley, Manjula Sunkara, Madan K Kharel, Andrew J Morris, James C Hower, Matthew S Tremblay, Mark A Prendergast, Jon S Thorson J Nat Prod. 2017 Jan 27;80(1):2-11. doi: 10.1021/acs.jnatprod.6b00948. Epub 2016 Dec 28.
The isolation and structure elucidation of six new bacterial metabolites [spoxazomicin D (2), oxachelins B and C (4, 5), and carboxamides 6-8] and 11 previously reported bacterial metabolites (1, 3, 9-12a, and 14-18) from Streptomyces sp. RM-14-6 is reported. Structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry data analysis, along with direct comparison to synthetic standards for 2, 11, and 12a,b. Complete 2D NMR assignments for the known metabolites lenoremycin (9) and lenoremycin sodium salt (10) were also provided for the first time. Comparative analysis also provided the basis for structural revision of several previously reported putative aziridine-containing compounds [exemplified by madurastatins A1, B1, C1 (also known as MBJ-0034), and MBJ-0035] as phenol-dihydrooxazoles. Bioactivity analysis [including antibacterial, antifungal, cancer cell line cytotoxicity, unfolded protein response (UPR) modulation, and EtOH damage neuroprotection] revealed 2 and 5 as potent neuroprotectives and lenoremycin (9) and its sodium salt (10) as potent UPR modulators, highlighting new functions for phenol-oxazolines/salicylates and polyether pharmacophores.
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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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