Paulomycin A2
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| Category | Antibiotics |
| Catalog number | BBF-02375 |
| CAS | 101411-68-1 |
| Molecular Weight | 786.80 |
| Molecular Formula | C34H46N2O17S |
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Description
It is produced by the strain of Str. paulus 273. It has anti-gram-positive bacteria effect, and it has inhibitory effect on staphylococcus aureus resistant to penicillin, streptomycin, neomycin and macrolide antibiotics. The antibacterial activity of Paulomycin A, A1 and B are stronger than other components.
Specification
| Synonyms | 1-Cyclohexene-1-carboxylic acid, 5-[6-O-acetyl-3-O-[2,6-dideoxy-3-O-methyl-4-C-[(S)-1-(3-methyl-1-oxobutoxy)ethyl]-α-L-lyxo-hexopyranosyl]-4-O-[(Z)-2-isothiocyanato-1-oxo-2-buten-1-yl]-β-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-, (5S)- |
| IUPAC Name | (3S)-3-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3-hydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyl-5-[(1S)-1-(3-methylbutanoyloxy)ethyl]oxan-2-yl]oxy-5-[(Z)-2-isothiocyanatobut-2-enoyl]oxyoxan-2-yl]-2,3-dihydroxy-6-imino-5-oxocyclohexene-1-carboxylic acid |
| Canonical SMILES | CC=C(C(=O)OC1C(OC(C(C1OC2CC(C(C(O2)C)(C(C)OC(=O)CC(C)C)O)OC)O)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)COC(=O)C)N=C=S |
| InChI | InChI=1S/C34H46N2O17S/c1-8-18(36-13-54)32(44)53-27-20(12-48-17(6)37)51-30(33(45)11-19(38)25(35)24(29(33)41)31(42)43)26(40)28(27)52-23-10-21(47-7)34(46,16(5)50-23)15(4)49-22(39)9-14(2)3/h8,14-16,20-21,23,26-28,30,35,40-41,45-46H,9-12H2,1-7H3,(H,42,43)/b18-8-,35-25?/t15-,16-,20+,21-,23-,26+,27+,28-,30+,33+,34+/m0/s1 |
| InChI Key | HNDRMNSKDIUAHQ-DNHCBWAZSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 888.0°C at 760 mmHg |
| Melting Point | 95-105°C (dec.) |
| Density | 1.49 g/cm3 |
| Solubility | Soluble in Hydrochloric acid, Sodium hydroxide |
Reference Reading
1. Characterization of a 3-hydroxyanthranilic acid 6-hydroxylase involved in paulomycin biosynthesis
Yong Ding, Min Wang, Jine Li, Pengwei Li, Zhenyan Guo, Yihua Chen Biochem Biophys Res Commun. 2021 Mar 5;543:8-14. doi: 10.1016/j.bbrc.2021.01.042. Epub 2021 Jan 23.
Paulomycins (PAUs) refer to a group of glycosylated antibiotics with attractive antibacterial activities against Gram-positive bacteria. They contain a special ring A moiety that is prone to dehydrate between C-4 and C-5 to a quinone-type form at acidic condition, which will reduce the antibacterial activities of PAUs significantly. Elucidation of the biosynthetic mechanism of the ring A moiety may facilitate its structure modifications by combinatorial biosynthesis to generate PAU analogues with enhanced bioactivity or stability. Previous studies showed that the ring A moiety is derived from chorismate, which is converted to 3-hydroxyanthranilic acid (3-HAA) by a 2-amino-2-deoxyisochorismate (ADIC) synthase, a 2,3-dihydro-3-hydroxyanthranilic acid (DHHA) synthase, and a DHHA dehydrogenase. Unfortunately, little is known about the conversion process from 3-HAA to the highly decorated ring A moiety of PAUs. In this work, we characterized Pau17 as an unprecedented 3-HAA 6-hydroxylase responsible for the conversion of 3-HAA to 3,6-DHAA by in vivo and in vitro studies, pushing one step forward toward elucidating the biosynthetic mechanism of the ring A moiety of PAUs.
2. New paulomycins produced by Streptomyces paulus
A D Argoudelis, L Baczynskyj, W J Haak, W M Knoll, S A Mizsak, F B Shilliday J Antibiot (Tokyo). 1988 Feb;41(2):157-69. doi: 10.7164/antibiotics.41.157.
Paulomycin A2 (C34H46N2O17S), paulomycin C (C32H42N2O17S), paulomycin D (C31H40N2O17S), paulomycin E (C29H36N2O16S) and paulomycin F (C29H38N2O16S) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined using NMR and mass spectroscopic techniques. The new paulomycins, like paulomycins A and B (J. Antibiotics 35: 285-294, 1982) are highly active mainly against Gram-positive organisms.
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Bio Calculators
* 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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
