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O-Demethylpaulomycin A

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O-Demethylpaulomycin A
Category Antibiotics
Catalog number BBF-00830
CAS 113603-74-0
Molecular Weight 772.77
Molecular Formula C33H44N2O17S

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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

O-Demethylpaulomycin A is a quinone antibiotic produced by Streptomyces paulus. It has the effect of anti-gram-positive bacteria, and its activity is lower than that of Pauloycin.

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Synonyms 5-[6-(acetyloxymethyl)-4-[4,5-dihydroxy-6-methyl-5-[1-(2-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-3-hydroxy-5-[(E)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2-amino-5-hydroxy-3,6-dioxocyclohexene-1-carboxylic acid; 1-Cyclohexene-1-carboxylic acid, 5-(6-O-acetyl-3-O-(2,6-dideoxy-4-C-((S(S))-1-(2-methyl-1-oxobutoxy)ethyl)-alpha-L-lyxo-hexopyranosyl)-4-O-((Z)-2-isothiocyanato-1-oxo-2-butenyl)-beta-D-allopyranosyl)-2-amino-5-hydroxy-3,6-dioxo-, (S)-
IUPAC Name 3-[6-(acetyloxymethyl)-4-[4,5-dihydroxy-6-methyl-5-[1-(2-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-3-hydroxy-5-[(E)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid
Canonical SMILES CCC(C)C(=O)OC(C)C1(C(OC(CC1O)OC2C(C(OC(C2OC(=O)C(=CC)N=C=S)COC(=O)C)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)O)C)O
InChI InChI=1S/C33H44N2O17S/c1-7-13(3)30(43)49-15(5)33(46)14(4)48-21(9-20(33)38)51-26-24(39)28(32(45)10-18(37)23(34)22(27(32)40)29(41)42)50-19(11-47-16(6)36)25(26)52-31(44)17(8-2)35-12-53/h8,13-15,19-21,24-26,28,34,38-40,45-46H,7,9-11H2,1-6H3,(H,41,42)/b17-8+,34-23?
InChI Key MMHXEYFKFMVGKP-MIRXUTFGSA-N
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 899.9°C at 760 mmHg
Density 1.54 g/cm3
1. O-demethylpaulomycins A and B, U-77,802 and U-77,803, paulomenols A and B, new metabolites produced by Streptomyces paulus
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday J Antibiot (Tokyo). 1988 Oct;41(10):1316-30. doi: 10.7164/antibiotics.41.1316.
O-Demethylpaulomycin A (C33H44N2O17S), O-demethylpaulomycin B (C32H42N2O17S), paulomenol A (C29H43NO16), paulomenol B (C28H41NO16), and the hydrogen sulfide adducts of paulomycin A (U-77,802, C34H48N2O17S2), and paulomycin B (U-77,803, C33H46N2O17S2) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined by 1H and 13C NMR and fast atom bombardment mass spectrum spectroscopic techniques and degradative studies. The antibacterial properties of these new metabolites, which are related to paulomycins A and B (J. Antibiotics 35: 285-294, 1982), are briefly discussed.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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