Carbomycin

Carbomycin
Names

IUPAC name (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(3R,7R,8S,9S,10R,12R,14E)-7-Acetoxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy}-4-(dimethylamino)-5-hydr oxy-2-methyltetrahydro-2H-pyran-3-yl]oxy}-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate
Identifiers
CAS Number	4564-87-8
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1231649
ChemSpider	4450165
PubChem	5287879
InChI InChI=1S/C42H67NO16/c1-21(2)16-32(47)57-40-25(6)53-34(20-42(40,8)50)58-37-24(5)54-41(36(49)35(37)43(9)10)59-38-27(14-15-44)17-22(3)28(46)12-13-29-30(56-29)18-23(4)52-33(48)19-31(39(38)51-11)55-26(7)45/h12-13,15,21-25,27,29-31,34-41,49-50H,14,16-20H2,1-11H3/b13-12+/t22-,23-,24-,25+,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1 Key: FQVHOULQCKDUCY-OGHXVOSASA-N InChI=1/C42H67NO16/c1-21(2)16-32(47)57-40-25(6)53-34(20-42(40,8)50)58-37-24(5)54-41(36(49)35(37)43(9)10)59-38-27(14-15-44)17-22(3)28(46)12-13-29-30(56-29)18-23(4)52-33(48)19-31(39(38)51-11)55-26(7)45/h12-13,15,21-25,27,29-31,34-41,49-50H,14,16-20H2,1-11H3/b13-12+/t22-,23-,24-,25+,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1 Key: FQVHOULQCKDUCY-OGHXVOSABQ
SMILES C[C@@H]1C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O[C@@H](C[C@H]2[C@@H](O2)/C=C/C1=O)C)OC(=O)C)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C)O[C@H]4C[C@@]([C@H]([C@@H](O4)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O
Properties
Chemical formula	C₄₂H₆₇NO₁₆
Molar mass	841.97848
Density	1.24g/ cm3
Melting point	214℃ (417.2°F)
Basicity (pK_b)	7.2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carbomycin, also known as magnamycin, is a colorless, optically active crystallinemacrolide antibiotic with the molecular formula C₄₂H₆₇N O₁₆. It is derived from the bacterium Streptomyces halstedii and active in inhibiting the growth of Gram-positive bacteria and "certain Mycoplasma strains." Its structure was first proposed by Robert Woodward in 1957 and was subsequently corrected in 1965.

The discovery of carbomycin was first reported by Fred W. Tanner Jr. of Pfizer. Carbomycin can be isolated from Streptomyces halstedii via extraction from a fermentation broth and purified through crystallization from alcohol-water mixtures. Carbomycin can be further purified with the use of preparative thin-layer chromatography. The most efficient solvent is one consisting of ethanol-hexane-water in 90-10-0.15 volume ratio.

In the biosynthesis of carbomycin by Streptomyces halstedii, when soybean meal is used to ferment the antibiotic, the addition of several substances can increase the yield of carbomycin. When blackstrap molasses, a carbon source, is added, an increased yield is observed. Nitrogen sources ammonium chloride, ammonium nitrate, and ammonium dihydrogen phosphate have the same effect on the production of carbomycin. The addition of the organic salts sodium acetate and sodium tartrate also increases the yield of the antibiotic.

Studies of the chemical degradation of carbomycin and comparison of molar activities of propionate-labeled carbomycins and their degradation products suggest that the biosynthesis of carbomycin by Streptomyces halstedii include the synthesis of the lactone backbone from eight acetate units and one propionate unit with the branching methyl group deriving from C-3 of propionate.

...
Wikipedia