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Demethylolivomycin A

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Category Antibiotics
Catalog number BBF-00826
CAS 86917-61-5
Molecular Weight 1183.24
Molecular Formula C57H82O26

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Demethylolivomycin A is an antitumor antibiotic produced by Streptomyces aburaviensis. It has anti-Gram-positive bacteria and anti-leukemia P388 activity.

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Synonyms Olivomycin D, 4B-O-demethyl-3D-(2,6-dideoxy-3-C-methyl-4-O-(2-methyl-1-oxopropyl)-alpha-L-arabino-hexapyranosyl)-
IUPAC Name [6-[6-[6-[[6-[5-acetyloxy-4-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-6-methyloxan-2-yl]oxy-3-(3,4-dihydroxy-1-methoxy-2-oxopentyl)-8,9-dihydroxy-1-oxo-3,4-dihydro-2H-anthracen-2-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]oxy-3-hydroxy-2-methyloxan-4-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 2-methylpropanoate
Canonical SMILES CC1C(C(CC(O1)OC2CC(OC(C2OC(=O)C)C)OC3=CC(=C4C(=C3)C=C5CC(C(C(=O)C5=C4O)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)OC(=O)C(C)C)(C)O)C(C(=O)C(C(C)O)O)OC)O)O)O
InChI InChI=1S/C57H82O26/c1-21(2)56(69)83-55-27(8)76-42(20-57(55,10)70)80-36-17-40(73-24(5)48(36)65)79-35-18-41(74-25(6)47(35)64)82-54-32(53(71-11)51(68)45(62)22(3)58)14-30-12-29-13-31(15-33(60)43(29)49(66)44(30)50(54)67)78-39-19-37(52(26(7)75-39)77-28(9)59)81-38-16-34(61)46(63)23(4)72-38/h12-13,15,21-27,32,34-42,45-48,52-55,58,60-66,70H,14,16-20H2,1-11H3
InChI Key ZIUTZULQAIKKKE-UHFFFAOYSA-N
Appearance Orange Powder
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 1165.9°C at 760 mmHg
Melting Point 163.4-165.1°C
Density 1.44 g/cm3
1. New aureolic acid antibiotics. II. Structure determination
M Koenuma, Y Yoshimura, K Matsumoto, Y Terui J Antibiot (Tokyo). 1988 Jan;41(1):68-72. doi: 10.7164/antibiotics.41.68.
Structure determination using NMR spectroscopy of new aureolic acid analogues, demethylchromomycins A2 and A3 and demethylolivomycins A and B produced by Streptomyces aburaviensis PA-39856, is described.
2. NMR studies of chromomycins, olivomycins, and their derivatives
Y Yoshimura, M Koenuma, K Matsumoto, K Tori, Y Terui J Antibiot (Tokyo). 1988 Jan;41(1):53-67. doi: 10.7164/antibiotics.41.53.
Detailed studies on the 13C and 1H NMR spectra of chromomycins A2 and A3, olivomycins A and B, and their derivatives clarified the assignment of many signals which had been unassigned or erroneously reported in the literatures. The revised assignments for chromomycin A3 and olivomycin A include the assignment of a key 13C signal used to discuss the saccharide linkage in question. Structure analyses based on the revised assignments support the alpha,1----3-bond between components of the disaccharide moiety in the molecules. Some general information useful for structure analysis of saccharides is also reported.

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