Fumaramidmycin

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Fumaramidmycin
Category Antibiotics
Catalog number BBF-01852
CAS 57687-92-0
Molecular Weight 232.23
Molecular Formula C12H12N2O3
Purity ≥98%

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Description

An antibiotic originally isolated from Streptomyces kurssanovii NR-7GG1. It has the activity against gram-positive bacteria and negative bacteria (individual).

Specification

Synonyms Antibiotic C 9154; trans-N-(Phenylacetyl)-2-butenediamide; Ro 09-0049; N1-(2-phenylacetyl)fumaramide
IUPAC Name (E)-N'-(2-phenylacetyl)but-2-enediamide
Canonical SMILES C1=CC=C(C=C1)CC(=O)NC(=O)C=CC(=O)N
InChI InChI=1S/C12H12N2O3/c13-10(15)6-7-11(16)14-12(17)8-9-4-2-1-3-5-9/h1-7H,8H2,(H2,13,15)(H,14,16,17)/b7-6+
InChI Key RPPKWABVORYKHA-VOTSOKGWSA-N

Properties

Appearance Colorless Crystalline
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 510.8°C at 760 mmHg
Melting Point 202-203°C
Density 1.25 g/cm3
Solubility Soluble in DMF, DMSO

Reference Reading

1. A new antibiotic, fumaramidmycin. II. Isolation, structure and syntheses
Y Suhara, H B Maruyama, Y Koto, Y Miyasaka, K Yokose J Antibiot (Tokyo). 1975 Sep;28(9):648-55. doi: 10.7164/antibiotics.28.648.
A new antibiotic fumaramidmycin produced by Streptomyces kurssanovii NR-7GG1 was isolated as colorless crystals. The structure was shown to be N-(phenylacetyl) fumaramide. Starting from fumaramic acid, fumaramidmycin has been synthesized in good yield, in which the key stage involves N-acylated imino ether formation followed by mild acid hydrolysis. Five analogues of fumaramidmycin have also been prepared.
2. A new antibiotic, fumaramidmycin I. Production, biological properties and characterization of producer strain
H B Maruyama, Y Suhara, J Suzuki-Watanabe, Y Maeshima, N Shimizu J Antibiot (Tokyo). 1975 Sep;28(9):636-47. doi: 10.7164/antibiotics.28.636.
A new antibiotic, fumaramidmycin, has been isolated from a streptomycete NR-7GG1 which was characterized and named Streptomyces kurssanovii. The strain produced the antibiotic only when grown on agar plates but not in the submerged culture broth, where the contact with the vegetative mycelia appears to cause the inactivation of the antibiotic. The antibiotic shows an antimicrobial activity against both Gram-positive and Gram-negative bacteria.

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