Altromycin A

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Altromycin A
Category Antibiotics
Catalog number BBF-00429
CAS 128439-47-4
Molecular Weight 911.94
Molecular Formula C46H57NO18
Purity 95%

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It is produced by the strain of Actinomycetes AB 1246E-26. It has anti-Gram-positive bacteria activity, and the MIC for Streptococcus and Staphylococcus is between 0.2-3.12ug/mL. It also has an inhibitory effect on a variety of tumor cells.


Synonyms methyl 2-(3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)-2-(2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-10-(5-((5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)-4,6-dimethyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)-4,7,12-trioxo-7,12-dihydro-4H-naphtho[2,3-h]chromen-5-yl)-2-hydroxyacetate; D-glycero-D-manno-Octonicacid,3,7-anhydro-8-deoxy-2-C-[2-(2,3-dimethyloxiranyl)-7,12-dihydro-11-hydroxy-4,7,12-trioxo-10-[2,3,6-trideoxy-4-O-(2,6-dideoxy-3-O-methyl-a-D-ribo-hexopyranosyl)-3-C-methyl-3-(methylamino)-a-L-lyxo-hexopyranosyl]-4H-anthra[1,2-b]pyran-5-yl]-5-O-methyl-,methyl ester, (2x)-(9CI); 4H-Anthra[1,2-b]pyran, D-glycero-D-manno-octonic acid deriv.
IUPAC Name methyl 2-[(2S,3S,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]-2-[2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-10-[(2R,4S,5S,6S)-5-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyl-4-(methylamino)oxan-2-yl]-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxyacetate
Canonical SMILES CC1C(C(CC(O1)OC2C(OC(CC2(C)NC)C3=C(C4=C(C=C3)C(=O)C5=CC(=C6C(=O)C=C(OC6=C5C4=O)C7(C(O7)C)C)C(C8C(C(C(C(O8)C)O)OC)O)(C(=O)OC)O)O)C)OC)O
InChI InChI=1S/C46H57NO18/c1-17-33(49)26(57-8)15-29(61-17)64-41-19(3)60-27(16-44(41,5)47-7)21-11-12-22-30(36(21)52)37(53)31-23(35(22)51)13-24(32-25(48)14-28(63-39(31)32)45(6)20(4)65-45)46(56,43(55)59-10)42-38(54)40(58-9)34(50)18(2)62-42/h11-14,17-20,26-27,29,33-34,38,40-42,47,49-50,52,54,56H,15-16H2,1-10H3/t17-,18-,19+,20?,26+,27-,29-,33-,34-,38+,40-,41-,42+,44+,45?,46?/m1/s1


Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 1021.3 °C at 760 mmHg
Density 1.470 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Altromycins, novel pluramycin-like antibiotics. I. Taxonomy of the producing organism, fermentation and antibacterial activity
M Jackson, J P Karwowski, R J Theriault, D J Hardy, S J Swanson, G J Barlow, P M Tillis, J B McAlpine J Antibiot (Tokyo). 1990 Mar;43(3):223-8. doi: 10.7164/antibiotics.43.223.
The altromycins are novel anthraquinone-derived antibiotics related to the pluramycins. They are produced by an actinomycete, AB 1246E-26, which was isolated from a South African bushveld soil. The altromycins have Gram-positive antibacterial activity with MICs of 0.2 to 3.12 micrograms/ml against Streptococci and Staphylococci.
2. Synthesis of the aglycones of altromycins and kidamycin from a common intermediate
ZhongBo Fei, Frank E McDonald Org Lett. 2005 Aug 18;7(17):3617-20. doi: 10.1021/ol0509742.
The aglycone structures 1 and 2, respectively corresponding to the antitumor antibiotic natural products altromycin and kidamycin, have been efficiently synthesized from a common advanced intermediate 3. A series of Claisen condensations and aromatizations affords the anthracene section of 3, followed by annulation of the pyrone ring. The functional groups of 3 can be manipulated for enantioselective introduction of the epoxide side-chain of altromycin aglycone 1, as well as synthesis of the kidamycin aglycone 2. [reaction: see text]
3. Altromycins, novel pluramycin-like antibiotics. II. Isolation and elucidation of structure
G M Brill, J B McAlpine, D N Whittern, A M Buko J Antibiot (Tokyo). 1990 Mar;43(3):229-37. doi: 10.7164/antibiotics.43.229.
A novel complex of Gram-positive antibiotics was produced from the fermentation of an actinomycete culture AB 1246E-26. The antibiotics were recovered from the whole fermentation broth by extraction with organic solvent and isolated using counter-current chromatography. UV and IR data place these compounds in the anthraquinone-derived class of antibiotics. Mass spectral and NMR data indicate a new complex of compounds related to, but distinctly different from the pluramycin type antibiotics.

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