Neutramycin
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| Category | Antibiotics |
| Catalog number | BBF-02602 |
| CAS | 1404-08-6 |
| Molecular Weight | 686.78 |
| Molecular Formula | C34H54O14 |
| Purity | 95% |
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Description
It is produced by the strain of Str. rimosus NRRL 3016. Neutramycin is resistant to gram-positive bacteria.
Specification
| Synonyms | Neutramycina; Neutramycinum; 6-Demethylchalcomycin; (1S,2E,5S,8S,9S,10E,14R,15R,16S)-5-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-8-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,9,14-trimethyl-13,17-dioxabicyclo[14.1.0]heptadeca-2,10-diene-4,12-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,3R,6E,8S,9S,12S,14E,16S)-12-hydroxy-2-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-9-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,8,12-trimethyl-4,17-dioxabicyclo[14.1.0]heptadeca-6,14-diene-5,13-dione |
| Canonical SMILES | CC1CC(C(C(O1)OC2CCC(C(=O)C=CC3C(O3)C(C(OC(=O)C=CC2C)C)COC4C(C(C(C(O4)C)O)OC)OC)(C)O)O)OC |
| InChI | InChI=1S/C34H54O14/c1-17-9-12-26(36)45-19(3)21(16-43-33-31(42-8)30(41-7)27(37)20(4)46-33)29-23(47-29)10-11-25(35)34(5,39)14-13-22(17)48-32-28(38)24(40-6)15-18(2)44-32/h9-12,17-24,27-33,37-39H,13-16H2,1-8H3/b11-10+,12-9+/t17-,18+,19+,20+,21+,22-,23-,24-,27+,28+,29-,30+,31+,32-,33+,34-/m0/s1 |
| InChI Key | RZLRMVZBGPHYJA-XXJPCBNGSA-N |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 222-223°C |
| Density | 1.26g/cm3 |
Reference Reading
1. Genomic and Secondary Metabolite Analyses of Streptomyces sp. 2AW Provide Insight into the Evolution of the Cycloheximide Pathway
Elizabeth R Stulberg, Gabriel L Lozano, Jesse B Morin, Hyunjun Park, Ezra G Baraban, Christine Mlot, Christopher Heffelfinger, Gillian M Phillips, Jason S Rush, Andrew J Phillips, Nichole A Broderick, Michael G Thomas, Eric V Stabb, Jo Handelsman Front Microbiol. 2016 May 3;7:573. doi: 10.3389/fmicb.2016.00573. eCollection 2016.
The dearth of new antibiotics in the face of widespread antimicrobial resistance makes developing innovative strategies for discovering new antibiotics critical for the future management of infectious disease. Understanding the genetics and evolution of antibiotic producers will help guide the discovery and bioengineering of novel antibiotics. We discovered an isolate in Alaskan boreal forest soil that had broad antimicrobial activity. We elucidated the corresponding antimicrobial natural products and sequenced the genome of this isolate, designated Streptomyces sp. 2AW. This strain illustrates the chemical virtuosity typical of the Streptomyces genus, producing cycloheximide as well as two other biosynthetically unrelated antibiotics, neutramycin, and hygromycin A. Combining bioinformatic and chemical analyses, we identified the gene clusters responsible for antibiotic production. Interestingly, 2AW appears dissimilar from other cycloheximide producers in that the gene encoding the polyketide synthase resides on a separate part of the chromosome from the genes responsible for tailoring cycloheximide-specific modifications. This gene arrangement and our phylogenetic analyses of the gene products suggest that 2AW holds an evolutionarily ancestral lineage of the cycloheximide pathway. Our analyses support the hypothesis that the 2AW glutaramide gene cluster is basal to the lineage wherein cycloheximide production diverged from other glutarimide antibiotics. This study illustrates the power of combining modern biochemical and genomic analyses to gain insight into the evolution of antibiotic-producing microorganisms.
2. Purification, structure determination, and antimicrobial activity of neutramycins B-G
Edmund I Graziani, Cassia R Overk, Guy T Carter J Nat Prod. 2003 Sep;66(9):1149-53. doi: 10.1021/np0301691.
Neutramycins B-G were purified from a historical sample of neutramycin in our antibiotic collection. The structures of the compounds were solved by 2D NMR spectroscopic analysis. Four of the compounds (2-5) are probable biosynthetic intermediates or shunt metabolites of neutramycin biosynthesis, while two (6, 7) are likely to be degradation products. Only one intermediate (5) showed weak Gram-positive activity.
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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 ╳
