Synonym
Lactenocin; Demycarosylmacrocin;
IUPAC/Chemical Name
2-((4R,5S,6S,7S,9S,11Z,13E,15S,16R)-15-((((2S,3S,4S,5R,6R)-4,5-dihydroxy-3-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-6-(((2R,3S,4S,5R,6S)-4-(dimethylamino)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-16-ethyl-4-hydroxy-5,9,13-trimethyl-2,10-dioxooxacyclohexadeca-11,13-dien-7-yl)acetaldehyde
InChi Key
CFMSCYSETWZXRS-QVZFMMNHSA-N
InChi Code
InChI=1S/C38H63NO14/c1-10-28-25(18-49-38-36(48-9)34(47)32(45)23(6)51-38)15-19(2)11-12-26(41)20(3)16-24(13-14-40)35(21(4)27(42)17-29(43)52-28)53-37-33(46)30(39(7)8)31(44)22(5)50-37/h11-12,14-15,20-25,27-28,30-38,42,44-47H,10,13,16-18H2,1-9H3/b12-11-,19-15+/t20-,21-,22-,23+,24+,25-,27+,28+,30-,31-,32-,33-,34-,35+,36-,37-,38-/m0/s1
SMILES Code
C[C@@H](C[C@H]([C@H](O[C@@H]1O[C@H]([C@H](O)[C@H](N(C)C)[C@@H]1O)C)[C@H]([C@H](O)CC(O[C@@H]2CC)=O)C)CC=O)C(/C=C\C(C)=C\[C@H]2CO[C@@H](O[C@H](C)[C@H](O)[C@@H]3O)[C@H]3OC)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
757.91
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
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2: Seno ET, Pieper RL, Huber FM. Terminal stages in the biosynthesis of tylosin. Antimicrob Agents Chemother. 1977 Mar;11(3):455-61. PubMed PMID: 855999; PubMed Central PMCID: PMC352007.
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4: Kim E, Song MC, Kim MS, Beom JY, Lee EY, Kim DM, Nam SJ, Yoon YJ. Characterization of the Two Methylation Steps Involved in the Biosynthesis of Mycinose in Tylosin. J Nat Prod. 2016 Aug 26;79(8):2014-21. doi: 10.1021/acs.jnatprod.6b00267. Epub 2016 Jul 25. PubMed PMID: 27453999.
5: Zuzulova M, Kleinova D, Proksa B, Fuska J. In vitro activity of tylosin and its derivatives against Ureaplasma urealyticum. Arzneimittelforschung. 1995 Nov;45(11):1222-4. PubMed PMID: 8929244.
6: Kreuzman AJ, Turner JR, Yeh WK. Two distinctive O-methyltransferases catalyzing penultimate and terminal reactions of macrolide antibiotic (tylosin) biosynthesis. Substrate specificity, enzyme inhibition, and kinetic mechanism. J Biol Chem. 1988 Oct 25;263(30):15626-33. PubMed PMID: 3170602.
7: Debono M, Willard KE, Kirst HA, Wind JA, Crouse GD, Tao EV, Vicenzi JT, Counter FT, Ott JL, Ose EE, et al. Synthesis and antimicrobial evaluation of 20-deoxo-20-(3,5-dimethylpiperidin-1-yl)desmycosin (tilmicosin, EL-870) and related cyclic amino derivatives. J Antibiot (Tokyo). 1989 Aug;42(8):1253-67. PubMed PMID: 2668243.
