U-77802

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Category Bioactive by-products
Catalog number BBF-01578
CAS 118625-41-5
Molecular Weight 820.9
Molecular Formula C34H48N2O17S2

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Description

Paulomycin A is a metabolite produced by Streptomyces paulus strain 273. It exhibits mild activity against gram-positive bacteria.

Specification

Synonyms U-77802; U-77,802; U 77802; U 77,802
IUPAC Name 3-[6-(acetyloxymethyl)-3-hydroxy-4-[5-hydroxy-4-methoxy-6-methyl-5-[1-(2-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-5-(5-methyl-2-sulfanylidene-1,3-thiazolidine-4-carbonyl)oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid
Canonical SMILES CCC(C)C(=O)OC(C)C1(C(OC(CC1OC)OC2C(C(OC(C2OC(=O)C3C(SC(=S)N3)C)COC(=O)C)C4(CC(=O)C(=N)C(=C4O)C(=O)O)O)O)C)O
InChI InChI=1S/C34H48N2O17S2/c1-8-12(2)30(43)50-15(5)34(46)14(4)49-20(9-19(34)47-7)52-26-24(39)28(33(45)10-17(38)22(35)21(27(33)40)29(41)42)51-18(11-48-16(6)37)25(26)53-31(44)23-13(3)55-32(54)36-23/h12-15,18-20,23-26,28,35,39-40,45-46H,8-11H2,1-7H3,(H,36,54)(H,41,42)
InChI Key NDTVBSYQVXVGSK-UHFFFAOYSA-N

Properties

Appearance Crystal
Antibiotic Activity Spectrum Gram-positive bacteria

Reference Reading

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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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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