Dactylocycline D

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Category Bioactive by-products
Catalog number BBF-00782
CAS 146064-00-8
Molecular Weight 740.15
Molecular Formula C33H42ClN3O14

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Description

Dactylocycline is a tetracycline antibiotic produced by Dactylospoangium sp.. Dactylocycline D has anti-Gram-positive bacteria activity.

Specification

Synonyms 6-((4-(acetoxyamino)-5-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-chloro-4-(dimethylamino)-3,4a,10,12,12a-pentahydroxy-8-methoxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
Storage Store at -20°C
IUPAC Name [[6-[[9-carbamoyl-4-chloro-7-(dimethylamino)-1,6a,10,10a,12-pentahydroxy-3-methoxy-5-methyl-8,11-dioxo-6,7-dihydro-5aH-tetracen-5-yl]oxy]-3-methoxy-2,4-dimethyloxan-4-yl]amino] acetate
Canonical SMILES CC1C(C(CC(O1)OC2(C3CC4(C(C(=O)C(=C(C4(C(=O)C3=C(C5=C2C(=C(C=C5O)OC)Cl)O)O)O)C(=O)N)N(C)C)O)C)(C)NOC(=O)C)OC
InChI InChI=1S/C33H42ClN3O14/c1-12-28(48-8)30(3,36-51-13(2)38)11-17(49-12)50-31(4)14-10-32(45)25(37(5)6)24(41)20(29(35)44)27(43)33(32,46)26(42)18(14)23(40)19-15(39)9-16(47-7)22(34)21(19)31/h9,12,14,17,25,28,36,39-40,43,45-46H,10-11H2,1-8H3,(H2,35,44)
InChI Key VFTDFPDDNYOKOT-UHFFFAOYSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 839.8°C at 760 mmHg
Density 1.56 g/cm3
Solubility Soluble in DMSO

Reference Reading

1. Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. II. Structure elucidation
A A Tymiak, H A Ax, M S Bolgar, A D Kahle, M A Porubcan, N H Andersen J Antibiot (Tokyo). 1992 Dec;45(12):1899-906. doi: 10.7164/antibiotics.45.1899.
Fermentation of Dactylosporangium sp. (ATCC 53693) produces a mixture of tetracycline derivatives from which several related tetracycline glycosides, the dactylocyclines, were isolated and their structures determined. The most abundant glycoside in initial fermentations was found to be dactylocycline A. Each glycoside proved to be acid sensitive and readily hydrolyzed to a common aglycone, dactylocyclinone. While the aglycone was cross resistant with tetracycline, the dactylocyclines proved active against certain tetracycline-resistant organisms.

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