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MedKoo Cat#: 571074 | Name: Rutamycin

Description:

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

Rutamycin, also known as Oligomycin D, is a macrolide antibiotic of the oligomycin group, obtained from Streptomyces rutgersensis. It is used in cytochemistry as a tool to inhibit various ATPases and to uncouple oxidative phosphorylation from electron transport. Clinically, it may be used as an antifungal agent.

Chemical Structure

Rutamycin
Rutamycin
CAS#1404-59-7

Theoretical Analysis

MedKoo Cat#: 571074

Name: Rutamycin

CAS#: 1404-59-7

Chemical Formula: C44H72O11

Exact Mass: 776.5075

Molecular Weight: 777.05

Elemental Analysis: C, 68.01; H, 9.34; O, 22.65

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 #
No Data
Synonym
Rutamycin; Oligomycin D; A 272; A272; A-272
IUPAC/Chemical Name
(1S,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-((R)-2-hydroxypropyl)-5',6,8,10,12,14,16,29-octamethyl-3',4',5',6'-tetrahydro-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-pyran]-4,18,20-triene-3,9,13-trione
InChi Key
LVWVMRBMGDJZLM-BONFEJLISA-N
InChi Code
InChI=1S/C44H72O11/c1-11-33-16-14-12-13-15-27(4)41(50)43(10,52)42(51)32(9)40(49)31(8)39(48)30(7)38(47)26(3)17-20-37(46)53-36-24-44(54-34(19-18-33)29(36)6)22-21-25(2)35(55-44)23-28(5)45/h12-14,16-17,20,25-36,38,40-41,45,47,49-50,52H,11,15,18-19,21-24H2,1-10H3/b13-12+,16-14+,20-17+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41-,43+,44-/m0/s1
SMILES Code
CC[C@@H]1CC[C@@H]2O[C@]3(CC[C@H](C)[C@H](C[C@@H](C)O)O3)C[C@H](OC(=O)\C=C\[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@](C)(O)[C@@H](O)[C@H](C)C\C=C\C=C\1)[C@@H]2C
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
>2 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 777.05 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: Lichtor T, Getz GS. Cytoplasmic inheritance of rutamycin resistance in mouse fibroblasts. Proc Natl Acad Sci U S A. 1978 Jan;75(1):324-8. PubMed PMID: 146879; PubMed Central PMCID: PMC411240. 2: Panek JS, Jain NF. Total synthesis of rutamycin B and oligomycin C. J Org Chem. 2001 Apr 20;66(8):2747-56. PubMed PMID: 11304197. 3: Foury F, Tzagoloff A. Localization on mitochondrial DNA of mutations leading to a loss of rutamycin-sensitive adenosine triphosphatase. Eur J Biochem. 1976 Sep;68(1):113-9. PubMed PMID: 134892. 4: White JD, Hanselmann R, Jackson RW, Porter WJ, Ohba Y, Tiller T, Wang S. Total synthesis of rutamycin B, a macrolide antibiotic from Streptomyces aureofaciens. J Org Chem. 2001 Jul 27;66(15):5217-31. PubMed PMID: 11463276. 5: Lichtor T, Tung B, Getz GS. Cytoplasmically inherited respiratory deficiency of a mouse fibroblast line which is resistant to rutamycin. Biochemistry. 1979 Jun 12;18(12):2582-90. PubMed PMID: 444478. 6: Pradelli LA, Villa E, Zunino B, Marchetti S, Ricci JE. Glucose metabolism is inhibited by caspases upon the induction of apoptosis. Cell Death Dis. 2014 Sep 4;5:e1406. doi: 10.1038/cddis.2014.371. PubMed PMID: 25188516; PubMed Central PMCID: PMC4540195. 7: Fisher RJ, Liang AM, Sundstrom GC. Selective disaggregation of the H+-translocating ATPase. Isolation of two discrete complexes of the rutamycin-insensitive ATPase differing in mitochondrial membrane-binding properties. J Biol Chem. 1981 Jan 25;256(2):707-15. PubMed PMID: 6450207. 8: LARDY HA, WITONSKY P, JOHNSON D. ANTIBIOTICS AS TOOLS FOR METABOLIC STUDIES. IV. COMPARATIVE EFFECTIVENESS OF OLIGOMYCINS A, B, C, AND RUTAMYCIN AS INHIBITORS OF PHOSPHORYL TRANSFER REACTIONS IN MITOCHONDRIA. Biochemistry. 1965 Mar;4:552-4. PubMed PMID: 14311628. 9: Schmitt M, Rittinghaus K, Scheurich P, Schwulera U, Dose K. Immunological properties of membrane-bound adenosine triphosphatase: immunological identification of rutamycin-sensitive F0.F1ATPase from Micrococcus luteus ATCC 4698 established by crossed immunoelectrophoresis. Biochim Biophys Acta. 1978 Jun 2;509(3):410-8. PubMed PMID: 77681. 10: Racker E. Preparation of reconstitutively active rutamycin-sensitive ATPase from bovine heart mitochondria. Methods Enzymol. 1979;55:315-7. PubMed PMID: 156836. 11: MICHEL R, HUET P, HUET M. [ACTION OF RUTAMYCIN (A-272) ON HEPATIC METOCHONDRIAL ADENOSINE TRIPHOSPHATASE IN RATS]. C R Seances Soc Biol Fil. 1964;158:994-8. French. PubMed PMID: 14234621. 12: Ozawa T, Hagihara M, Yamanaka N, Yagi K. Mitochondrial protein biosynthesis insensitive to arsenate or rutamycin. Arch Biochem Biophys. 1970 Feb;136(2):585-7. PubMed PMID: 5435449. 13: Van Dop C, Hutson SM, Lardy HA. Pyruvate metabolism in bovine epididymal spermatozoa. J Biol Chem. 1977 Feb 25;252(4):1303-8. PubMed PMID: 838718. 14: Tzagoloff A. Assembly of the mitochondrial membrane system. IV. Role of mitochondrial and cytoplasmic protein synthesis in the biosynthesis of the rutamycin-sensitive adenosine triphosphatase. J Biol Chem. 1971 May 10;246(9):3050-6. PubMed PMID: 4251997. 15: Tzagoloff A, Meagher P. Assesmbly of the mitochondrial membrane system. VI. Mitochondrial synthesis of subunit proteins of the rutamycin-sensitive adenosine triphosphatase. J Biol Chem. 1972 Jan 25;247(2):594-603. PubMed PMID: 4257924. 16: Stuart KD. Cytoplasmic inheritance of oligomycin and rutamycin resistance in yeast. Biochem Biophys Res Commun. 1970;39(6):1045-51. PubMed PMID: 5513244. 17: Tzagoloff A, Meagher P. Assembly of the mitochondrial membrane system. V. Properties of a dispersed preparation of the rutamycin-sensitive adenosine triphosphatase of yeast mitochondria. J Biol Chem. 1971 Dec 10;246(23):7328-36. PubMed PMID: 4256832. 18: Koch G. Synthesis of the mitochondrial inner membrane in cultured Xenopus laevis oocytes. J Biol Chem. 1976 Oct 10;251(19):6097-107. PubMed PMID: 184093. 19: Bulos B, Racker E. Partial resolution of the enzymes catalyzing oxidative phosphorylation. XVII. Further resolution of the rutamycin-sensitive adenosine triphosphatase. J Biol Chem. 1968 Jul 25;243(14):3891-900. PubMed PMID: 4233195. 20: Beechey RB, Williams V, Holloway CT, Knight IG, Roberton AM. Estimation of the molecular weights and molecular formulae of oligomycin-A, rutamycin & aurovertin by mass spectrometry. Biochem Biophys Res Commun. 1967 Feb 8;26(3):339-41. PubMed PMID: 6034358.