Dactylocycline A
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| Category | Antibiotics |
| Catalog number | BBF-00780 |
| CAS | 125622-12-0 |
| Molecular Weight | 698.11 |
| Molecular Formula | C31H40ClN3O13 |
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Description
Dactylocycline is a tetracycline antibiotic produced by Dactylospoangium sp.. Dactylocycline A has anti-Gram-positive bacteria and weak anti-Gram-negative bacteria activity, and is not cross-resistant with tetracycline-resistant bacteria.
Specification
| Synonyms | 7-chloro-4-(dimethylamino)-3,4a,10,12,12a-pentahydroxy-6-((4-(hydroxyamino)-5-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-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 | 7-chloro-4-(dimethylamino)-1,4a,10,11,12a-pentahydroxy-6-[4-(hydroxyamino)-5-methoxy-4,6-dimethyloxan-2-yl]oxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4H-tetracene-2-carboxamide |
| 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)NO)OC |
| InChI | InChI=1S/C31H40ClN3O13/c1-11-26(46-7)28(2,34-44)10-15(47-11)48-29(3)12-9-30(42)23(35(4)5)22(38)18(27(33)41)25(40)31(30,43)24(39)16(12)21(37)17-13(36)8-14(45-6)20(32)19(17)29/h8,11-12,15,23,26,34,36-37,40,42-44H,9-10H2,1-7H3,(H2,33,41) |
| InChI Key | TUXHICHKDSJQIG-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 845.3°C at 760 mmHg |
| Density | 1.59 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Water, Acetonitrile |
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.
2. Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. III. Absolute stereochemistry of the dactylocyclines
P V Devasthale, L A Mitscher, H Telikepalli, D Vander Velde, J Y Zou, H A Ax, A A Tymiak J Antibiot (Tokyo). 1992 Dec;45(12):1907-13. doi: 10.7164/antibiotics.45.1907.
The dactylocycline antibiotics were found through circular dichroism measurements, NMR spectroscopy and chemical transformations to possess the usual tetracycline family absolute configuration at carbons 4, 4a, 5a and 12a. The absolute stereochemistry about the C-6 carbon, however, was the reverse of that found with previously investigated tetracyclines.
3. Heterologous expression and manipulation of three tetracycline biosynthetic pathways
Peng Wang, Woncheol Kim, Lauren B Pickens, Xue Gao, Yi Tang Angew Chem Int Ed Engl. 2012 Oct 29;51(44):11136-40. doi: 10.1002/anie.201205426. Epub 2012 Sep 28.
A very accommodating host: Three tetracycline biosynthetic pathways were overexpressed and manipulated in the heterologous host Streptomyces lividans K4-114. Through the inactivation of various genes and characterization of the resulting biosynthetic intermediates, new tetracycline-modifying enzymes were identified (see scheme).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
