Tylosin
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| Category | Antibiotics |
| Catalog number | BBF-03431 |
| CAS | 1401-69-0 |
| Molecular Weight | 916.10 |
| Molecular Formula | C46H77NO17 |
| Purity | >98% |
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Description
Tylosin is a 16-member-ring macrolide produced through the fermentation of Streptomyces fradiae, a species of actinobacteria found in soil. It is effective against gram-positive bacteria, Mycoplasma species and certain gram-negative bacteria. With other macrolides, tylosin inhibits protein synthesis by binding to the 50S subunit of the bacterial ribosome and disrupting aminoacyl-and peptidyl-tRNA transcription. This is believed to ultimately prevent the bacteria from reproducing.
Specification
| Related CAS | 11032-12-5 (hydrochloride) |
| Synonyms | Tylosine; Tylocine; Tylosinum; Fradizine; NSC758961; (10E,12E)-(3R,4S,5S,6R,8R,14S,15R)-14-((6-deoxy-2,3-di-O-methyl-beta-D-allopyranosyl)oxymethyl)-5-((3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-dimethylamino-beta-D-glucopyranosyl)oxy)-6-formylmethyl-3-hydroxy-4,8,12-trimethyl-9-oxoheptadeca-10,12-dien-15-olide |
| Storage | Store at-20°C |
| IUPAC Name | 2-[(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde |
| Canonical SMILES | CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)C)COC4C(C(C(C(O4)C)O)OC)OC |
| InChI | InChI=1S/C46H77NO17/c1-13-33-30(22-58-45-42(57-12)41(56-11)37(52)26(5)60-45)18-23(2)14-15-31(49)24(3)19-29(16-17-48)39(25(4)32(50)20-34(51)62-33)64-44-38(53)36(47(9)10)40(27(6)61-44)63-35-21-46(8,55)43(54)28(7)59-35/h14-15,17-18,24-30,32-33,35-45,50,52-55H,13,16,19-22H2,1-12H3/b15-14+,23-18+/t24-,25+,26-,27-,28+,29+,30-,32-,33-,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46-/m1/s1 |
| InChI Key | WBPYTXDJUQJLPQ-VMXQISHHSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycoplasma |
| Boiling Point | 980.7°C at 760 mmHg |
| Melting Point | 127-132°C |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Moderater water solubility. |
Reference Reading
1. Effects of Matrix and Functional Groups on Tylosin Adsorption onto Resins and Carbon Nanotubes
Yipin Lu & Miao Jiang & Chuanwei Wang. Water Air Soil Pollut (2013) 224:1536
Tylosin is a bulky molecule expected to induce the size-exclusion effect upon adsorption onto microporous adsorbents. Ji et al. (2010a) proposed that the adsorption of bulky tylosin is lower onto activated carbons with more micropores than onto synthesized carbons with more mesopores because of the size-exclusion effect. Fu et al. (2011) noted that commercial microporous-activated carbon treated with potassium hydroxide activation markedly increases the specific surface area and enlarges the pore sizes of the mesopores. The adsorption of tylosin is greatly increased by more than one order of magnitude due to the enhanced size-exclusion effect. Obvious size-exclusion effects were also found in the adsorption of other bulky organic chemicals. Ji et al. (2009) observed that the adsorbent-to-solution distribution coef-ficient (Kd, in liter/kilogram) of tetracycline is in the order of 104 to 106 L/kg for single-wall nanotube (SWNT), 103 to 104 L/kg for multiwall nanotube (MWNT), 103 to 104 L/kg for activated carbon (AC), and 103 to 105 L/kg for graphite. Upon normalization of the adsorbent surface area, the adsorption affinity of tetracycline decreases in the following order: graphite/SWNT > MWNT > AC. The weaker adsorption of tetracycline onto AC indicates that for bulky adsorbates, adsorption affinity is caused by the molecular sieving effect. Liu et al. (2006) found that the maximum adsorption amount of nonylphenol ethoxylates (NPE) over activated carbon is approximately 350 mg g−1, which was markedly lower than that of mesoporous carbon CMK-3.
2. Expression of tyIM genes during tylosin production: Phantom promoters and enigmatic translational coupling motifs
SA Flint, G Stratigopoulos, AR Butler and E Cundliffe. Journal of Industrial Microbiology & Biotechnology (2002) 28, 160 – 167
Complementation of tylM-KO strains with tylM DNA
None of the three tylM-KO strains accumulated macrolide material when fermented in tylosin production medium (Figures 3a, 4a and 5a) although, as expected, each could produce tylosin when complemented with a block of wild type DNA containing tyl[MIII–MII–MI ] under control of the strong, constitutive promoter, ermEp* ( see Figures 3b and 5b). Note, however, that wild type levels of tylosin production were not achieved by the complemented strains (compare Figure 3b and d), since the C31 attB site, used for integration of complementing DNA, is not a neutral site in the context of tylosin production. Thus, integration of the ‘‘empty’’ vector, pLST9828, into that site reduces tylosin yields by up to 50% (unpublished data; this laboratory). Note also that it was not necessary to include the ccr gene (Figure 1), downstream of and codirectional with the tylM genes, in the blocks of complementing DNA, since strains lacking ccr can still produce tylosin.
3. Influence of dimethylsulfoxide on tylosin production in Streptomyces fradiae
AR Butler and E Cundliffe. Journal of Industrial Microbiology & Biotechnology (2001) 27, 46 – 51
As yet, relatively little is known about the regulation of macrolide biosynthesis nor is it yet obvious whether a common pattern of control might emerge. For example, the intensively studied erythromycin-biosynthetic ( ery ) gene cluster of Saccha-ropolyspora erythraea contains no regulatory genes and none that control erythromycin production has yet been identified elsewhere in the Sacc. erythraea genome. In contrast, the tylosin-biosynthetic ( tyl ) gene cluster of Streptomyces fradiae contains at least five candidate regulatory genes. Although the precise functions of the latter remain to be established, a current model proposes that tylosin production is controlled in pathway-specific fashion by regulatory protein( s ) of the SARP family and/or by the product of tylR and also by one or more gamma-butyrolactone signalling factors. The TylR protein appears to mediate global control of tylosin production, since both polyketide and deoxysugar metabolism were abolished in a tylR-disrupted strain of S. fradiae. As an added complication, glycosylated precursors of tylosin are required to stimulate production of the aglycone, tylactone. In this respect, glycosylated macrolides act catalytically ( in an uncharacterized manner ) to turn a trickle of polyketide metabolism into a flood. However, none of this implies that the polyketide aglycone and the three tylosin sugars are necessarily produced in stoichiometrically equivalent amounts. The primary purpose of the present work was to address this point and to determine whether tylosin production in S. fradiae is limited by availability of the aglycone or of the sugars. It was also of interest to ascertain whether such limitation has changed significantly during the empirical selection of enhanced production strains.
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Bio Calculators
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