10-Decarbomethoxyaclacinomycin A

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Category Antibiotics
Catalog number BBF-02013
CAS 76264-91-0
Molecular Weight 753.83
Molecular Formula C40H51NO13

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Description

10-Decarbomethoxyaclacinomycin A is an anthracycline antibiotic produced by Streptomyces galilaeus MA144-Mlt mutant strain KE303. It has anti-tumor and gram-positive bacteria activity.

Specification

Synonyms 7-epi-10-Decarbomethoxyaclacinomycin A
IUPAC Name 7-[4-(dimethylamino)-5-[4-hydroxy-6-methyl-5-(6-methyl-5-oxooxan-2-yl)oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-4,6,9-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
Canonical SMILES CCC1(CC(C2=C(C3=C(C=C2C1)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
InChI InChI=1S/C40H51NO13/c1-7-40(48)16-21-13-23-34(37(47)33-22(35(23)45)9-8-10-26(33)43)36(46)32(21)28(17-40)52-30-14-24(41(5)6)38(19(3)50-30)54-31-15-27(44)39(20(4)51-31)53-29-12-11-25(42)18(2)49-29/h8-10,13,18-20,24,27-31,38-39,43-44,46,48H,7,11-12,14-17H2,1-6H3
InChI Key OXPCRXLITLBLEY-UHFFFAOYSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Boiling Point 876.9±65.0°C at 760 mmHg
Melting Point 139-141°C
Density 1.4±0.1 g/cm3

Reference Reading

1. Modification of aklavinone and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products
Yulong Wang, Jarmo Niemi, Pekka Mäntsälä FEMS Microbiol Lett. 2002 Feb 19;208(1):117-22. doi: 10.1111/j.1574-6968.2002.tb11070.x.
The rdm genes B, C and E from Streptomyces purpurascens encode enzymes that tailor aklavinone and aclacinomycins. We report that in addition to hydroxylation of aklavinone to epsilon-rhodomycinone, RdmE (aklavinone-11-hydroxylase) hydroxylated 11-deoxy-beta-rhodomycinone to beta-rhodomycinone both in vivo and in vitro. 15-Demethoxyaklavinone and decarbomethoxyaklavinone did not serve as substrates. RdmC (aclacinomycin methyl esterase) converted aclacinomycin T (AcmT) to 15-demethoxyaclacinomycin T, which was in turn converted to 10-decarbomethoxyaclacinomycin T and then to rhodomycin B by RdmB (aclacinomycin-10-hydroxylase). RdmC and RdmB were most active on AcmT, the one-sugar derivative, with their activity decreasing by 70-90% on two- and three-sugar aclacinomycins. Aclacinomycin A competitively inhibited the AcmT modifications at C-10. The results presented here suggest that in vivo the modifications at C-10 take place principally after addition of the first sugar.

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