Senfolomycin A
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| Category | Antibiotics |
| Catalog number | BBF-02900 |
| CAS | 11017-36-0 |
| Molecular Weight | 700.66 |
| Molecular Formula | C29H36N2O16S |
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Description
It is produced by the strain of Str. ochrosporus NRRL 3146. It has the effect of anti-Gram-positive bacteria and mycobacterium, and also has the effect of anti-Staphylococcus aureus resistant to penicillin, streptomycin, neomycin, macrolide antibiotics. It also has weaker effect of anti-Gram-negative bacteria.
Specification
| Related CAS | 101411-69-2 |
| Synonyms | Paulomycin E; 1-Cyclohexene-1-carboxylic acid, 5-[6-O-acetyl-3-O-(4-C-acetyl-2,6-dideoxy-3-O-methyl-a-L-xylo-hexopyranosyl)-4-O-[(2Z)-2-isothiocyanato-1-oxo-2-butenyl]-b-D-allopyranosyl]-2-amino-5-hydroxy-3,6-dioxo-, (5S)-; Antibiotic LL RA 6950BA |
| IUPAC Name | (3S)-3-[(2R,3R,4S,5R,6R)-4-[(2R,4S,5R,6S)-5-acetyl-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-(acetyloxymethyl)-3-hydroxy-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(=O)C)O)OC)O)C3(CC(=O)C(=N)C(=C3O)C(=O)O)O)COC(=O)C)N=C=S |
| InChI | InChI=1S/C29H36N2O16S/c1-6-14(31-10-48)27(39)47-22-16(9-43-13(4)33)45-25(28(40)8-15(34)20(30)19(24(28)36)26(37)38)21(35)23(22)46-18-7-17(42-5)29(41,11(2)32)12(3)44-18/h6,12,16-18,21-23,25,30,35-36,40-41H,7-9H2,1-5H3,(H,37,38)/b14-6-,30-20?/t12-,16+,17-,18-,21+,22+,23-,25+,28+,29+/m0/s1 |
| InChI Key | YASNRWMRDSCJIV-BBGPBDROSA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria |
| Boiling Point | 878.9°C at 760 mmHg |
| Melting Point | 122-124°C |
| Density | 1.58 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Ethanol |
Reference Reading
1. Structural relationships between senfolomycins and paulomycins
A D Argoudelis, L Baczynskyj, S A Mizsak, F B Shilliday, P F Wiley J Antibiot (Tokyo). 1988 Sep;41(9):1212-22. doi: 10.7164/antibiotics.41.1212.
Senfolomycins A and B (Antimicrob. Agents Chemother.-1965: 828-831, 1966) are two antibacterial agents with physico-chemical and biological properties similar to those of paulomycin. Recent studies indicate that senfolomycin A (C29H36N2O16S, MW 700) has molecular composition and fast atom bombardment MS fragmentation pattern identical to those of paulomycin E. Extensive NMR work indicates that the two antibiotics, which have been separated by HPLC and TLC, differ only in the stereochemistry of the OCH3 group present in their respective sugar moieties. Indirect evident suggests that senfolomycin B is dihydrosenfolomycin A (C29H38N2O16S, MW 702) and in this respect it is related to paulomycin F. The proposed structures for senfolomycins A and B are discussed.
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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 ╳
