Altromycin B

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Altromycin B
Category Antibiotics
Catalog number BBF-00430
CAS 128461-00-7
Molecular Weight 925.96
Molecular Formula C47H59NO18
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 GTPL10964; Octonic acid, 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-alpha-D-ribo-hexopyranosyl)-3-(dimethylamino)-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-4H-anthra(1,2-b)pyran-5-yl)-5-O-methyl-, methyl ester; 4H-Anthra[1,2-b]pyran,D-glycero-D-manno-octonic acid deriv.; 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-(dimethylamino)-3-C-methyl-a-L-lyxo-hexopyranosyl]-4H-anthra[1,2-b]pyran-5-yl]-5-O-methyl-,methyl ester, (2x)-
IUPAC Name methyl 2-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)-2-[10-[4-(dimethylamino)-5-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-4,6-dimethyloxan-2-yl]-2-(2,3-dimethyloxiran-2-yl)-11-hydroxy-4,7,12-trioxonaphtho[2,3-h]chromen-5-yl]-2-hydroxyacetate
Canonical SMILES CC1C(C(CC(O1)OC2C(OC(CC2(C)N(C)C)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/C47H59NO18/c1-18-34(50)27(58-9)16-30(62-18)65-42-20(3)61-28(17-45(42,5)48(7)8)22-12-13-23-31(37(22)53)38(54)32-24(36(23)52)14-25(33-26(49)15-29(64-40(32)33)46(6)21(4)66-46)47(57,44(56)60-11)43-39(55)41(59-10)35(51)19(2)63-43/h12-15,18-21,27-28,30,34-35,39,41-43,50-51,53,55,57H,16-17H2,1-11H3


Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 1018.2 °C at 760 mmHg
Density 1.460 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Synthesis of both possible isomers of the northwest quadrant of altromycin B
Paolo Pasetto, Richard W Franck J Org Chem. 2003 Oct 17;68(21):8042-60. doi: 10.1021/jo034607k.
The synthesis of the northwest quadrant of Altromycin B is described. The preparation of the two epimers at the quaternary carbon of the 6-deoxy-C-altrose moiety in the northwest quadrant is accomplished starting from d-glucose. A key step of our synthetic sequence is the formation of the C-glycoside linkage via the Ramberg-Bäcklund reaction. Two different routes are explored, which differ mainly on the timing of the conversion of glucose to altrose, either before or after the preparation of the C-glycoside. The conformation behavior of variously substituted C-altropyranoside rings is also discussed.
2. Synthesis of the branched C-glycoside substructure of altromycin B
Bonsuk Koo, Frank E McDonald Org Lett. 2005 Aug 18;7(17):3621-4. doi: 10.1021/ol050975u.
Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]
3. Fischer carbene catalysis of alkynol cycloisomerization: application to the synthesis of the altromycin B disaccharide
Bonsuk Koo, Frank E McDonald Org Lett. 2007 Apr 26;9(9):1737-40. doi: 10.1021/ol070435s. Epub 2007 Mar 27.
[reaction: see text] The tungsten-catalyzed cycloisomerization of alkynyl alcohols can be conducted without using photochemistry, using a stable tungsten Fischer carbene as the precatalyst for this transformation. A variety of alkynyl alcohols undergo cycloisomerization under these conditions to provide endocyclic enol ethers of five-, six-, and seven-membered ring sizes. The utility of this method is further demonstrated in the stereoselective synthesis of the disaccharide substructure of altromycin B.

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