Global InformationCarbomycin information
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| IUPAC name
[(1S,3R,7R,8S,9S,10R,12R,14E,16S)-7-(Acetyloxy)-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl 3,6-dideoxy-3-(dimethylamino)-β-D-glucopyranosid-4-O-yl] 2,6-dideoxy-3-C-methyl-α-L-ribo-hexopyranoside 4-(3-methylbutanoate)
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| Systematic IUPAC name
(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(1S,3R,7R,8S,9S,10R,12R,14E,16S)-7-(Acetyloxy)-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-hydroxy-2-methyloxan-2-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate | |
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| Properties | |
Chemical formula
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C42H67NO16 |
| Molar mass | 841.97848 |
| Density | 1.24g/ cm3 |
| Melting point | 214°C (417.2°F) |
| Basicity (pKb) | 7.2 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Carbomycin, also known as magnamycin, is a colorless, optically active crystalline[1] macrolide 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."[2] Its structure was first proposed by Robert Woodward in 1957 and was subsequently corrected in 1965.[3]
- ^ Wagner, Richard L.; F.A. Hochstein; Kotaro Murai; N. Messina; Peter P. Regna (1953). "Magnamycin. A new Antibiotic". J. Am. Chem. Soc. 75 (19): 4684–87. doi:10.1021/ja01115a019.
- ^ Ziegler, F. E.; Gilligan, P. J. (1981). "Synthetic Studies on the Carbomycins (Magnamycins): An Exception to the Enantioselective Synthesis of Beta-Alkyl Carboxylic Acids via Chiral Oxazolines". J. Org. Chem. 46 (19): 3874–80. doi:10.1021/jo00332a023.
- ^ Woodward, R. B.; Weiler, L. S.; Dutta, P. C. (1965). "The Structure of Magnamycin". J. Am. Chem. Soc. 87 (20): 4662–63. doi:10.1021/ja00948a058. PMID 5845078.