Protylonolide

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

MedKoo CAT#: 462716

CAS#: 74758-60-4

Description: Protylonolide is a macrolide antibiotic. It is a macrolide ring that is the precursor of an antibiotic, tylosin.

Chemical Structure

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Protylonolide
CAS# 74758-60-4
Instruction

Theoretical Analysis

MedKoo Cat#: 462716
Name: Protylonolide
CAS#: 74758-60-4
Chemical Formula: C23H38O5
Exact Mass: 394.27
Molecular Weight: 394.552
Elemental Analysis: C, 70.02; H, 9.71; O, 20.27

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.

Request quote for custom synthesis

Synonym: Tylactone; 20-Dsdr;

IUPAC/Chemical Name: (11Z,13Z)-7,16-diethyl-4,6-dihydroxy-5,9,13,15-tetramethyloxacyclohexadeca-11,13-diene-2,10-dione

InChi Key: YJSXTLYNFBFHAT-WEJYHURQSA-N

InChi Code: InChI=1S/C23H38O5/c1-7-18-12-15(4)19(24)10-9-14(3)11-16(5)21(8-2)28-22(26)13-20(25)17(6)23(18)27/h9-11,15-18,20-21,23,25,27H,7-8,12-13H2,1-6H3/b10-9-,14-11-

SMILES Code: CCC1CC(C(/C=C\C(C)=C/C(C(OC(CC(C(C1O)C)O)=O)CC)C)=O)C

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 394.55 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: Omura S, Taki A, Matsuda K, Tanaka Y. Ammonium ions suppress the amino acid metabolism involved in the biosynthesis of protylonolide in a mutant of Streptomyces fradiae. J Antibiot (Tokyo). 1984 Nov;37(11):1362-9. doi: 10.7164/antibiotics.37.1362. PMID: 6511663.

2: Omura S, Tanaka Y, Mamada H, Masuma R. Effect of ammonium ion, inorganic phosphate and amino acids on the biosynthesis of protylonolide, a precursor of tylosin aglycone. J Antibiot (Tokyo). 1984 May;37(5):494-502. doi: 10.7164/antibiotics.37.494. PMID: 6735923.

3: Tanaka Y, Taki A, Masuma R, Omura S. Mechanism of nitrogen regulation of protylonolide biosynthesis in Streptomyces fradiae. J Antibiot (Tokyo). 1986 Jun;39(6):813-21. doi: 10.7164/antibiotics.39.813. PMID: 3733529.

4: Omura S, Sadakane N, Kitao C, Matsubara H, Nakagawa A. Production of mycarosyl protylonolide by a mycaminose idiotroph from the tylosin-producing strain Streptomyces fradiae KA-427. J Antibiot (Tokyo). 1980 Aug;33(8):913-4. doi: 10.7164/antibiotics.33.913. PMID: 7429996.

5: Sadakane N, Tanaka Y, Omura S. Hybrid biosynthesis of derivatives of protylonolide and M-4365 by macrolide-producing microorganisms. J Antibiot (Tokyo). 1982 Jun;35(6):680-7. doi: 10.7164/antibiotics.35.680. PMID: 7118724.

6: Omura S, Matsubara H, Nakagawa A, Furusaki A, Matsumoto T. X-ray crystallography of protylonolide and absolute configuration of tylosin. J Antibiot (Tokyo). 1980 Aug;33(8):915-7. doi: 10.7164/antibiotics.33.915. PMID: 7429997.

7: Butler AR, Cundliffe E. Influence of dimethylsulfoxide on tylosin production in Streptomyces fradiae. J Ind Microbiol Biotechnol. 2001 Jul;27(1):46-51. doi: 10.1038/sj.jim.7000160. PMID: 11598810.

8: Choi DB, Park Y, Okabe M. Effects of rapessed oil on activity of methylmalonyl-CoA carboxyltransferase in culture of Streptomyces fradiae. Biosci Biotechnol Biochem. 1998 May;62(5):902-6. doi: 10.1271/bbb.62.902. PMID: 9648221.

9: Butler AR, Flint SA, Cundliffe E. Feedback control of polyketide metabolism during tylosin production. Microbiology (Reading). 2001 Apr;147(Pt 4):795-801. doi: 10.1099/00221287-147-4-795. PMID: 11283275.

10: Jones ND, Chaney MO, Kirst HA, Wild GM, Baltz RH, Hamill RL, Paschal JW. Novel fermentation products from Streptomyces fradiae: X-ray crystal structure of 5-O-mycarosyltylactone and proof of the absolute configuration of tylosin. J Antibiot (Tokyo). 1982 Apr;35(4):420-5. doi: 10.7164/antibiotics.35.420. PMID: 7096197.

11: Lowell AN, DeMars MD 2nd, Slocum ST, Yu F, Anand K, Chemler JA, Korakavi N, Priessnitz JK, Park SR, Koch AA, Schultz PJ, Sherman DH. Chemoenzymatic Total Synthesis and Structural Diversification of Tylactone-Based Macrolide Antibiotics through Late-Stage Polyketide Assembly, Tailoring, and C-H Functionalization. J Am Chem Soc. 2017 Jun 14;139(23):7913-7920. doi: 10.1021/jacs.7b02875. Epub 2017 Jun 5. PMID: 28525276; PMCID: PMC5532807.

12: Bate N, Bignell DR, Cundliffe E. Regulation of tylosin biosynthesis involving 'SARP-helper' activity. Mol Microbiol. 2006 Oct;62(1):148-56. doi: 10.1111/j.1365-2958.2006.05338.x. Epub 2006 Aug 30. PMID: 16942604.

13: Kuhstoss S, Huber M, Turner JR, Paschal JW, Rao RN. Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene. 1996 Dec 12;183(1-2):231-6. doi: 10.1016/s0378-1119(96)00565-3. PMID: 8996112.

14: Castonguay R, Valenzano CR, Chen AY, Keatinge-Clay A, Khosla C, Cane DE. Stereospecificity of ketoreductase domains 1 and 2 of the tylactone modular polyketide synthase. J Am Chem Soc. 2008 Sep 3;130(35):11598-9. doi: 10.1021/ja804453p. Epub 2008 Aug 12. PMID: 18693734; PMCID: PMC2654278.

15: Omura S, Tsuzuki K, Tanaka Y, Sakakibara H, Aizawa M, Lukacs G. Valine as a precursor of n-butyrate unit in the biosynthesis of macrolide aglycone. J Antibiot (Tokyo). 1983 May;36(5):614-6. doi: 10.7164/antibiotics.36.614. PMID: 6874580.

16: Sadakane N, Tanaka Y, Omura S. Hybrid biosynthesis of a new macrolide antibiotic by a daunomycin-producing microorganism. J Antibiot (Tokyo). 1983 Jul;36(7):921-2. doi: 10.7164/antibiotics.36.921. PMID: 6885644.

17: 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.

18: Fish SA, Cundliffe E. Stimulation of polyketide metabolism in Streptomyces fradiae by tylosin and its glycosylated precursors. Microbiology (Reading). 1997 Dec;143 ( Pt 12):3871-6. doi: 10.1099/00221287-143-12-3871. PMID: 9421911.

19: Gaisser S, Reather J, Wirtz G, Kellenberger L, Staunton J, Leadlay PF. A defined system for hybrid macrolide biosynthesis in Saccharopolyspora erythraea. Mol Microbiol. 2000 Apr;36(2):391-401. doi: 10.1046/j.1365-2958.2000.01856.x. PMID: 10792725.

20: Dotzlaf JE, Metzger LS, Foglesong MA. Incorporation of amino acid-derived carbon into tylactone by Streptomyces fradiae GS14. Antimicrob Agents Chemother. 1984 Feb;25(2):216-20. doi: 10.1128/aac.25.2.216. PMID: 6424562; PMCID: PMC185477.