Corynecin II

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Corynecin II
Category Antibiotics
Catalog number BBF-01740
CAS 35098-52-3
Molecular Weight 268.27
Molecular Formula C12H16N2O5
Purity >99% by HPLC

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Description

It is produced by the strain of Corynebacterium KY-4339. It has weak activity against gram-positive bacteria and gram-negative bacteria.

Specification

Synonyms D-threo-1-p-Nitrophenyl-2-propionamido-1,3-propanediol; N-[(1R,2R)-2-Hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]propanamide; d-threo-2-(Propionamido)-1-(p-nitrophenyl)-1,3-propanediol
Storage -20 °C
IUPAC Name N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]propanamide
Canonical SMILES CCC(=O)NC(CO)C(C1=CC=C(C=C1)[N+](=O)[O-])O
InChI InChI=1S/C12H16N2O5/c1-2-11(16)13-10(7-15)12(17)8-3-5-9(6-4-8)14(18)19/h3-6,10,12,15,17H,2,7H2,1H3,(H,13,16)/t10-,12-/m1/s1
InChI Key LJMULVALRTTYIT-ZYHUDNBSSA-N
Source Corynebacterium sp.

Properties

Appearance White solid
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Melting Point 109-110 °C
Solubility Soluble in Ethyl Acetate, Methanol, Ethanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. Metabolites of a blocked chloramphenicol producer
Tamara L Adamek, Elizabeth A Lewis, Robert L White, Leo C Vining J Nat Prod . 2003 Jan;66(1):62-6. doi: 10.1021/np020306e.
Addition of p-aminophenylalanine (4), an advanced biosynthetic precursor of the antibiotic chloramphenicol (5), to a Streptomyces venezuelae pabAB mutant (VS629) restored chloramphenicol production and led to formation of the non-chlorinated analogue corynecin II (6) and four acetanilide derivatives: p-(acetylamino)phenylalanine (7), p-(acetylamino)benzyl alcohol (13), p-(acetylamino)benzoic acid (14), and p-(acetylamino)phenol (acetaminophen, 16). Metabolite structures were deduced from NMR and MS-MS data and established by chromatographic and spectroscopic comparisons with authentic samples. Reference compound 13 was synthesized by reducing the acid chloride of 14. Shunt pathways are proposed to account for the formation of the metabolites from p-aminophenylalanine.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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