Enteromycin carboxamide
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01235 |
| CAS | 998-90-3 |
| Molecular Weight | 187.15 |
| Molecular Formula | C6H9N3O4 |
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Description
It is produced by the strain of Str. sp. AO-126. It has anti-gram positive bacteria and negative bacteria activity.
Specification
| Synonyms | 3-(2-(Methyl-aci-nitro)acetamido)acrylamide; Acrylamide, 3-(2-(methyl-aci-nitro)acetamido)-; 3-(((Methyl-aci-nitro)acetyl)amino)-2-propenamide; 2-Propenamide, 3-(((methyl-aci-nitro)acetyl)amino)- |
| IUPAC Name | 2-[[(E)-3-amino-3-oxoprop-1-enyl]amino]-N-methoxy-2-oxoethanimine oxide |
| Canonical SMILES | CO[N+](=CC(=O)NC=CC(=O)N)[O-] |
| InChI | InChI=1S/C6H9N3O4/c1-13-9(12)4-6(11)8-3-2-5(7)10/h2-4H,1H3,(H2,7,10)(H,8,11)/b3-2+,9-4+ |
| InChI Key | WWUHEQGWFDDSQX-DSXPNFDZSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Glycine-derived nitronates bifurcate to O-methylation or denitrification in bacteria
Hai-Yan He, Katherine S Ryan Nat Chem. 2021 Jun;13(6):599-606. doi: 10.1038/s41557-021-00656-8. Epub 2021 Mar 29.
Natural products with rare functional groups are likely to be constructed by unique biosynthetic enzymes. One such rare functional group is the O-methyl nitronate, which can undergo [3 + 2] cycloaddition reactions with olefins in mild conditions. O-methyl nitronates are found in some natural products; however, how such O-methyl nitronates are assembled biosynthetically is unknown. Here we show that the assembly of the O-methyl nitronate in the natural product enteromycin carboxamide occurs via activation of glycine on a peptidyl carrier protein, followed by reaction with a diiron oxygenase to give a nitronate intermediate and then with a methyltransferase to give an O-methyl nitronate. Guided by the discovery of this pathway, we then identify related cryptic biosynthetic gene cassettes in other bacteria and show that these alternative gene cassettes can, instead, facilitate oxidative denitrification of glycine-derived nitronates. Altogether, our work reveals bifurcating pathways from a central glycine-derived nitronate intermediate in bacteria.
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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 ╳
