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MedKoo Cat#: 462713 | Name: Mycaminosyltylonolide

Description:

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

Mycaminosyltylonolide is a macrolide antibiotic.

Chemical Structure

Mycaminosyltylonolide
Mycaminosyltylonolide
CAS#61257-02-1

Theoretical Analysis

MedKoo Cat#: 462713

Name: Mycaminosyltylonolide

CAS#: 61257-02-1

Chemical Formula: C31H51NO10

Exact Mass: 597.3513

Molecular Weight: 597.75

Elemental Analysis: C, 62.29; H, 8.60; N, 2.34; O, 26.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
O-Mycaminosyltylonolide; Mycaminosyltylonolide;
IUPAC/Chemical Name
2-((4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-(((2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-16-ethyl-4-hydroxy-15-(hydroxymethyl)-5,9,13-trimethyl-2,10-dioxooxacyclohexadeca-11,13-dien-7-yl)acetaldehyde
InChi Key
WGUJDBLMJBJUQU-VKRLOHBMSA-N
InChi Code
InChI=1S/C31H51NO10/c1-8-25-22(16-34)13-17(2)9-10-23(35)18(3)14-21(11-12-33)30(19(4)24(36)15-26(37)41-25)42-31-29(39)27(32(6)7)28(38)20(5)40-31/h9-10,12-13,18-22,24-25,27-31,34,36,38-39H,8,11,14-16H2,1-7H3/b10-9+,17-13+/t18-,19+,20-,21+,22-,24-,25-,27+,28-,29-,30-,31+/m1/s1
SMILES Code
CC[C@H]1OC(C[C@H]([C@@H]([C@H]([C@H](C[C@H](C(/C=C/C(C)=C/[C@@H]1CO)=O)C)CC=O)O[C@@H]2O[C@@H]([C@H]([C@H](N(C)C)[C@H]2O)O)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

Preparing Stock Solutions

The following data is based on the product molecular weight 597.75 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
1: Sugawara A, Maruyama H, Shibusawa S, Matsui H, Hirose T, Tsutsui A, Froyman R, Ludwig C, Koebberling J, Hanaki H, Kleefeld G, Ōmura S, Sunazuka T. 5-O-Mycaminosyltylonolide antibacterial derivatives: design, synthesis and bioactivity. J Antibiot (Tokyo). 2017 Jul;70(8):878-887. doi: 10.1038/ja.2017.61. Epub 2017 May 31. PMID: 28559578. 2: Shishkina A, Makarov G, Tereshchenkov A, Korshunova G, Sumbatyan N, Golovin A, Svetlov M, Bogdanov A. Conjugates of amino acids and peptides with 5-o-mycaminosyltylonolide and their interaction with the ribosomal exit tunnel. Bioconjug Chem. 2013 Nov 20;24(11):1861-9. doi: 10.1021/bc400236n. Epub 2013 Oct 25. PMID: 24090034. 3: Yao RC, Mahoney DF. Enzyme immunoassay for macrolide antibiotics: characterization of an antibody to 23-amino-O-mycaminosyltylonolide. Appl Environ Microbiol. 1989 Jun;55(6):1507-11. doi: 10.1128/AEM.55.6.1507-1511.1989. PMID: 2764563; PMCID: PMC202895. 4: Karahalios P, Kalpaxis DL, Fu H, Katz L, Wilson DN, Dinos GP. On the mechanism of action of 9-O-arylalkyloxime derivatives of 6-O-mycaminosyltylonolide, a new class of 16-membered macrolide antibiotics. Mol Pharmacol. 2006 Oct;70(4):1271-80. doi: 10.1124/mol.106.026567. Epub 2006 Jul 27. PMID: 16873579. 5: Kageyama S, Tsuchiya T, Umezawa S. Synthesis of 3-deoxy-3,4-didehydro derivatives of 5-O-mycaminosyltylonolide, 5-O-(4-deoxymycaminosyl) tylonolide, and desmycosin. J Antibiot (Tokyo). 1993 Aug;46(8):1265-78. doi: 10.7164/antibiotics.46.1265. PMID: 8407589. 6: Kirst HA, Toth JE, Wind JA, Debono M, Willard KE, Molloy RM, Paschal JW, Ott JL, Felty-Duckworth AM, Counter FT. Synthesis, antimicrobial evaluation and structure-activity relationships within 23-modified derivatives of 5-O-mycaminosyltylonolide. J Antibiot (Tokyo). 1987 Jun;40(6):823-42. doi: 10.7164/antibiotics.40.823. PMID: 3610835. 7: Kajikawa N, Tsuchiya T, Umezawa S, Umezawa H. Syntheses of 23-C-alkylidene, and 23-N-containing derivatives of 5-O-mycaminosyltylonolide. J Antibiot (Tokyo). 1987 Apr;40(4):476-82. doi: 10.7164/antibiotics.40.476. PMID: 3583916. 8: Fu H, Marquez S, Gu X, Katz L, Myles DC. Synthesis and in vitro antibiotic activity of 16-membered 9-O-arylalkyloxime macrolides. Bioorg Med Chem Lett. 2006 Mar 1;16(5):1259-66. doi: 10.1016/j.bmcl.2005.11.061. Epub 2005 Dec 15. PMID: 16343900. 9: Korshunova GA, Sumbatian NV, Fedorova NV, Kuznetsova IV, Shishkina AV, Bogdanov AA. [Peptide derivatives of tylosin-related macrolides]. Bioorg Khim. 2007 Mar-Apr;33(2):235-44. Russian. doi: 10.1134/s1068162007020033. PMID: 17476984. 10: Creemer LC, Beier RC, Kiehl DE. Facile synthesis of tilmicosin and tylosin related haptens for use as protein conjugates. J Antibiot (Tokyo). 2003 May;56(5):481-7. doi: 10.7164/antibiotics.56.481. PMID: 12870814. 11: Kirst HA, Debono M, Toth JE, Truedell BA, Willard KE, Ott JL, Counter FT, Felty-Duckworth AM, Pekarek RS. Synthesis and antimicrobial evaluation of acyl derivatives of 16-membered macrolide antibiotics related to tylosin. J Antibiot (Tokyo). 1986 Aug;39(8):1108-22. doi: 10.7164/antibiotics.39.1108. PMID: 3759662. 12: Sumbatian NV, Kuznetsova IV, Karpenko VV, Fedorova NV, Chertkov VA, Korshunova GA, Bogdanov AA. [Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified at the aldehyde group]. Bioorg Khim. 2010 Mar-Apr;36(2):265-76. Russian. doi: 10.1134/s1068162010020159. PMID: 20531486. 13: Kirst HA, Ose EE, Toth JE, Willard KE, Debono M, Felty-Duckworth AM, Pekarek RS. In vitro and in vivo evaluation of C-20- and C-23-modified derivatives of tylosin against veterinary pathogens. J Antibiot (Tokyo). 1988 Jul;41(7):938-48. doi: 10.7164/antibiotics.41.938. PMID: 3417566. 14: 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. 15: Chin NX, Neu HC. In vitro activity of MC-352, a new 16-membered macrolide. Antimicrob Agents Chemother. 1992 Aug;36(8):1699-702. doi: 10.1128/aac.36.8.1699. PMID: 1416853; PMCID: PMC192033. 16: von Eyken A, Bayen S. Non-targeted study of the thermal degradation of tylosin in honey, water and water:honey mixtures. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2020 Mar;37(3):421-437. doi: 10.1080/19440049.2019.1704442. Epub 2020 Jan 9. PMID: 31917648. 17: Kageyama S, Tsuchiya T, Umezawa S, Takeuchi T. Synthesis of 3,4'-dideoxymycaminosyl tylonolide, a novel type of macrolide derivative. J Antibiot (Tokyo). 1992 Jan;45(1):144-6. doi: 10.7164/antibiotics.45.144. PMID: 1548187. 18: Omura S, Tanaka H, Tsukui M. Biosynthesis of tylosin: oxidations of 5-O-mycaminosylprotylonolide at C-20 and C-23 with a cell-free extract from Streptomyces fradiae. Biochem Biophys Res Commun. 1982 Jul 30;107(2):554-60. doi: 10.1016/0006-291x(82)91527-3. PMID: 7126228. 19: Tanaka A, Tsuchiya T, Umezawa S, Hamada M, Umezawa H. Syntheses of derivatives of 4'-deoxymycaminosyl tylonolide and mycaminosyl tylonolide modified AT C-23. J Antibiot (Tokyo). 1981 Oct;34(10):1377-80. doi: 10.7164/antibiotics.34.1377. PMID: 7309634. 20: Creemer LC, Toth JE, Kirst HA. Synthesis and in vitro antimicrobial activity of 3-keto 16-membered macrolides derived from tylosin. J Antibiot (Tokyo). 2002 Apr;55(4):427-36. doi: 10.7164/antibiotics.55.427. PMID: 12061552.