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U-58431

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U-58431
Category Mycotoxins
Catalog number BBF-01575
CAS 75533-14-1
Molecular Weight 294.26
Molecular Formula C13H14N2O6

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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

U-58431 is an antibiotic isolated from Streptomyces helicus (UC-5837), which is effective against gram-positive and gram-negative bateria, and more potently against streptococcus pneumoniae. It exhibits toxicity.

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IUPAC Name (1R,8R,10R,11R)-1,6,11-trihydroxy-4-imino-10-methyl-3-oxo-9-oxatricyclo[6.2.2.02,7]dodeca-2(7),5-diene-5-carboxamide
Canonical SMILES CC1C2(C(CC(O1)C3=C2C(=O)C(=N)C(=C3O)C(=O)N)O)O
InChI InChI=1S/C13H14N2O6/c1-3-13(20)5(16)2-4(21-3)6-8(13)11(18)9(14)7(10(6)17)12(15)19/h3-5,14,16-17,20H,2H2,1H3,(H2,15,19)/t3-,4-,5-,13+/m1/s1
InChI Key XGXZRIYLDVKOFX-CLBFDLSJSA-N
Appearance Orange-red Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Melting Point 156-157°C (dec.)
1. Constitution and absolute stereochemistry of the antibiotic sarubicin A
K Eckardt, D Tresselt, W Ihn, M Kajtár, J Angyán, L Radics, M Hollósi J Antibiot (Tokyo). 1983 Aug;36(8):976-9. doi: 10.7164/antibiotics.36.976.
By spectral (UV-VIS, IR, NMR, MS and CD) methods the quinone antibiotics sarubicin A and U-58,431 were shown to have identical constitution and stereochemistry. Chiroptical data and their theoretical analysis have settled the common absolute configuration as 5S, 6R, 8R, 10R.
2. Fermentation, isolation, characterization and structure of antibiotic U-58,431
L Slechta, C G Chidester, F Reusser J Antibiot (Tokyo). 1980 Sep;33(9):919-23. doi: 10.7164/antibiotics.33.919.
A new antibiotic U-58,431 has been isolated from the fermentation broth of Streptomyces helicus DIETZ and LI, sp. n. (UC-5837) and the structure of this antibiotic, namely, 6-amino-3,4,5,8-tetrahydro-4,9-dihydroxy-3-methyl-5,8-dioxo-1,4-ethano-1H-2-benzopyron-7-carboxamide has been determined by X-ray crystallography. The antibiotic inhibits a variety of Gram-positive and Gram-negative bacteria in vitro. However, it is toxic to mice and does not protect experimentally infected animals when administered at the maximum tolerated dose.

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