Macrocin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 462708

CAS#: 11049-15-3

Description: Macrocin is a macrolide antibiotic. Biosynthetically, it is produced from demethylmacrocin by demethylmacrocin O-methyltransferase and is converted to tylosin, an antibiotic used in veterinary medicine, by macrocin O-methyltransferase.

Chemical Structure

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Macrocin
CAS# 11049-15-3
Instruction

Theoretical Analysis

MedKoo Cat#: 462708
Name: Macrocin
CAS#: 11049-15-3
Chemical Formula: C45H75NO17
Exact Mass: 901.50
Molecular Weight: 902.085
Elemental Analysis: C, 59.92; H, 8.38; N, 1.55; O, 30.15

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Tylosin C; BRN 6468979;

IUPAC/Chemical Name: 2-((4R,5S,7R,9R,11E,13E,16R)-15-((((2R,3R,4R,5S,6R)-4,5-dihydroxy-3-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)-6-(((2R,3R,4R,5S,6R)-5-(((2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-4-(dimethylamino)-3-hydroxy-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: UFUYRGNJTFAODM-MIUQDMJTSA-N

InChi Code: InChI=1S/C45H75NO17/c1-12-32-29(21-57-44-41(56-11)38(53)36(51)25(5)59-44)17-22(2)13-14-30(48)23(3)18-28(15-16-47)39(24(4)31(49)19-33(50)61-32)63-43-37(52)35(46(9)10)40(26(6)60-43)62-34-20-45(8,55)42(54)27(7)58-34/h13-14,16-17,23-29,31-32,34-44,49,51-55H,12,15,18-21H2,1-11H3/b14-13+,22-17+/t23-,24+,25-,26-,27+,28+,29?,31-,32-,34+,35-,36-,37-,38-,39?,40-,41-,42+,43+,44-,45-/m1/s1

SMILES Code: CC[C@H]1OC(C[C@H]([C@@H](C([C@H](C[C@H](C(/C=C/C(C)=C/C1CO[C@@H]2O[C@@H]([C@H]([C@H]([C@H]2OC)O)O)C)=O)C)CC=O)O[C@@H]3O[C@@H]([C@H]([C@H](N(C)C)[C@H]3O)O[C@H]4C[C@@](O)([C@H]([C@@H](O4)C)O)C)C)C)O)=O

Appearance: Solid powder

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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 902.09 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Seno ET, Baltz RH. Properties of S-adenosyl-L-methionine:macrocin O-methyltransferase in extracts of Streptomyces fradiae strains which produce normal or elevated levels of tylosin and in mutants blocked in specific O-methylations. Antimicrob Agents Chemother. 1981 Sep;20(3):370-7. doi: 10.1128/aac.20.3.370. PMID: 7305323; PMCID: PMC181703.

2: Seno ET, Baltz RH. S-Adenosyl-L-methionine: macrocin O-methyltransferase activities in a series of Streptomyces fradiae mutants that produce different levels of the macrolide antibiotic tylosin. Antimicrob Agents Chemother. 1982 May;21(5):758-63. doi: 10.1128/aac.21.5.758. PMID: 7103455; PMCID: PMC182007.

3: Bauer NJ, Kreuzman AJ, Dotzlaf JE, Yeh WK. Purification, characterization, and kinetic mechanism of S-adenosyl-L-methionine:macrocin O-methyltransferase from Streptomyces fradiae. J Biol Chem. 1988 Oct 25;263(30):15619-25. PMID: 3170601.

4: Yeh WK, Bauer NJ, Dotzlaf JE. High-performance liquid chromatographic assay for S-adenosyl-L-methionine: macrocin O-methyltransferase. J Chromatogr. 1984 Apr 20;288(1):157-65. doi: 10.1016/s0021-9673(01)93690-8. PMID: 6725471.

5: Seno ET, Pieper RL, Huber FM. Terminal stages in the biosynthesis of tylosin. Antimicrob Agents Chemother. 1977 Mar;11(3):455-61. doi: 10.1128/aac.11.3.455. PMID: 855999; PMCID: PMC352007.

6: Baltz RH, Seno ET. Properties of Streptomyces fradiae mutants blocked in biosynthesis of the macrolide antibiotic tylosin. Antimicrob Agents Chemother. 1981 Aug;20(2):214-25. doi: 10.1128/aac.20.2.214. PMID: 7283418; PMCID: PMC181666.

7: 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. PMID: 3170602.

8: HAMILL RL, STARK WM. MACROCIN, A NEW ANTIBIOTIC, AND LACTENOCIN, AN ACTIVE DEGRADATION PRODUCT. J Antibiot (Tokyo). 1964 Jul;17:133-9. PMID: 14196285.

9: Yeh WK. Evolving enzyme technology for pharmaceutical applications: case studies. J Ind Microbiol Biotechnol. 1997 Nov-Dec;19(5-6):334-43. doi: 10.1038/sj.jim.2900437. PMID: 9451830.

10: 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. PMID: 27453999.

11: Baltz RH, Seno ET, Stonesifer J, Wild GM. Biosynthesis of the macrolide antibiotic tylosin. A preferred pathway from tylactone to tylosin. J Antibiot (Tokyo). 1983 Feb;36(2):131-41. doi: 10.7164/antibiotics.36.131. PMID: 6833128.

12: Baltz RH, McHenney MA, Cantwell CA, Queener SW, Solenberg PJ. Applications of transposition mutagenesis in antibiotic producing streptomycetes. Antonie Van Leeuwenhoek. 1997 Feb;71(1-2):179-87. doi: 10.1023/a:1000177808686. PMID: 9049029.

13: Fouces R, Mellado E, Díez B, Barredo JL. The tylosin biosynthetic cluster from Streptomyces fradiae: genetic organization of the left region. Microbiology (Reading). 1999 Apr;145 ( Pt 4):855-868. doi: 10.1099/13500872-145-4-855. PMID: 10220165.

14: Fishman SE, Cox K, Larson JL, Reynolds PA, Seno ET, Yeh WK, Van Frank R, Hershberger CL. Cloning genes for the biosynthesis of a macrolide antibiotic. Proc Natl Acad Sci U S A. 1987 Dec;84(23):8248-52. doi: 10.1073/pnas.84.23.8248. PMID: 3479787; PMCID: PMC299519.

15: Inouye M, Suzuki H, Takada Y, Muto N, Horinouchi S, Beppu T. A gene encoding mycinamicin III O-methyltransferase from Micromonospora griseorubida. Gene. 1994 Apr 8;141(1):121-4. doi: 10.1016/0378-1119(94)90138-4. PMID: 8163162.

16: Cox KL, Fishman SE, Larson JL, Stanzak R, Reynolds PA, Yeh WK, van Frank RM, Birmingham VA, Hershberger CL, Seno ET. The use of recombinant DNA techniques to study tylosin biosynthesis and resistance in Streptomyces fradiae. J Nat Prod. 1986 Nov-Dec;49(6):971-80. doi: 10.1021/np50048a002. PMID: 3572425.

17: Chen HC, Wilde F. The effect of dissolved oxygen and aeration rate on antibiotic production of Streptomyces fradiae. Biotechnol Bioeng. 1991 Mar 15;37(6):591-5. doi: 10.1002/bit.260370615. PMID: 18600649.

18: Ose EE, Tonkinson LV. Comparison of the antimycoplasma activity of two commercially available tylosin premixes. Poult Sci. 1985 Feb;64(2):287-93. doi: 10.3382/ps.0640287. PMID: 3991415.

19: Vu-Trong K, Gray PP. Continuous-culture studies on the regulation of tylosin biosynthesis. Biotechnol Bioeng. 1982 May;24(5):1093-103. doi: 10.1002/bit.260240506. PMID: 18546402.

20: 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. doi: 10.7164/antibiotics.42.1253. PMID: 2668243.