Rubradirin

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

MedKoo CAT#: 461542

CAS#: 11031-38-2

Description: Rubradirin is an antibiotic of complex chemical structure which is active vs. methicillin resistant staphylococci. It acts as a selective inhibitor of enzymatic peptide initiation.

Chemical Structure

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Rubradirin
CAS# 11031-38-2
Instruction

Theoretical Analysis

MedKoo Cat#: 461542
Name: Rubradirin
CAS#: 11031-38-2
Chemical Formula: C48H46N4O20
Exact Mass: 998.27
Molecular Weight: 998.900
Elemental Analysis: C, 57.72; H, 4.64; N, 5.61; O, 32.03

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: Rubradirin;

IUPAC/Chemical Name: A name could not be generated for this structure.

InChi Key: GBZJIWQNTNUYGZ-ARBZVXFDSA-N

InChi Code: InChI=1S/C48H46N4O20/c1-17-11-19(3)40(39(59)42(60)48(6)16-49-30-36(56)23-12-18(2)34(54)29(33(17)53)28(23)38(58)41(30)72-48)71-46(63)32-37(57)26(69-27-15-47(5,52(64)65)43(67-8)20(4)68-27)14-24(50-32)44(61)51-31-35(55)22-10-9-21(66-7)13-25(22)70-45(31)62/h9-14,19-20,27,39-40,43,49,54-55,57,59H,15-16H2,1-8H3,(H,51,61)/b17-11+/t19-,20-,27+,39-,40-,43+,47+,48+/m0/s1

SMILES Code: Oc1c(O[C@H]2O[C@@H](C)[C@@H](OC)[C@](C)(N(=O)=O)C2)cc(C(Nc(c(O)c3ccc(OC)cc3o4)c4=O)=O)nc1C(O[C@@H]5[C@H](O)C([C@]6(C)OC(C(c7c8cc(C)c(O)c7C(/C(C)=C/[C@@H]5C)=O)=O)=C(NC6)C8=O)=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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 998.90 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: Boll B, Heide L. A domain of RubC1 of rubradirin biosynthesis can functionally replace MbtH-like proteins in tyrosine adenylation. Chembiochem. 2013 Jan 2;14(1):43-4. doi: 10.1002/cbic.201200633. Epub 2012 Dec 6. PubMed PMID: 23225745.

2: Hoeksema H, Lewis C, Mizsak SA, Shiley JA, Wait DR, Whaley HA, Zurenko GE. The isolation and characterization of rubradirin B. J Antibiot (Tokyo). 1978 Oct;31(10):945-8. PubMed PMID: 711617.

3: Bannister B, Zapotocky BA. Protorubradirin, an antibiotic containing a C-nitroso-sugar fragment, is the true secondary metabolite produced by Streptomyces achromogenes var. rubradiris. Rubradirin, described earlier, is its photo-oxidation product. J Antibiot (Tokyo). 1992 Aug;45(8):1313-24. PubMed PMID: 1399853.

4: Kim CG, Lamichhane J, Song KI, Nguyen VD, Kim DH, Jeong TS, Kang SH, Kim KW, Maharjan J, Hong YS, Kang JS, Yoo JC, Lee JJ, Oh TJ, Liou K, Sohng JK. Biosynthesis of rubradirin as an ansamycin antibiotic from Streptomyces achromogenes var. rubradiris NRRL3061. Arch Microbiol. 2008 May;189(5):463-73. Epub 2007 Dec 14. PubMed PMID: 18080113.

5: Marshall VP, McWethy SJ, Sirotti JM, Cialdella JI. The effect of neutral resins on the fermentation production of rubradirin. J Ind Microbiol. 1990 Jul;5(5):283-7. PubMed PMID: 1366609.

6: Boll B, Hennig S, Xie C, Sohng JK, Heide L. Adenylate-forming enzymes of rubradirin biosynthesis: RubC1 is a bifunctional enzyme with aminocoumarin acyl ligase and tyrosine-activating domains. Chembiochem. 2011 May 2;12(7):1105-14. doi: 10.1002/cbic.201000778. Epub 2011 Mar 29. PubMed PMID: 21448870.

7: Reusser F. Inhibition of ribosomal and RNA polymerase functions by rubradirin and its aglycone. J Antibiot (Tokyo). 1979 Nov;32(11):1186-92. PubMed PMID: 393685.

8: Sohng JK, Oh TJ, Lee JJ, Kim CG. Identification of a gene cluster of biosynthetic genes of rubradirin substructures in S. achromogenes var. rubradiris NRRL3061. Mol Cells. 1997 Oct 31;7(5):674-81. PubMed PMID: 9387157.

9: Reusser F. Rubradirin, a selective inhibitor of initiation factor dependent peptide-chain initiation. Biochemistry. 1973 Oct 23;12(22):4524-8. PubMed PMID: 4584327.

10: MEYER CE. RUBRADIRIN, A NEW ANTIBIOTIC. II. ISOLATION AND CHARACTERIZATION. Antimicrob Agents Chemother (Bethesda). 1964;10:97-9. PubMed PMID: 14288039.

11: Maharjan J, Liou K, Lee HC, Kim CG, Lee JJ, Yoo JC, Sohng JK. Functional identification of rub52 gene involved in the biosynthesis of rubradirin. Biotechnol Lett. 2003 Jun;25(11):909-15. PubMed PMID: 12889805.

12: Mizsak SA, Hoeksema H, Pschigoda LM. The chemistry of rubradirin. II. Rubranitrose. J Antibiot (Tokyo). 1979 Jul;32(7):771-2. PubMed PMID: 541274.

13: BHUYAN BK, OWEN SP, DIETZ A. RUBRADIRIN, A NEW ANTIBIOTIC. I. FERMENTATION AND BIOLOGICAL PROPERTIES. Antimicrob Agents Chemother (Bethesda). 1964;10:91-6. PubMed PMID: 14288038.

14: Hoeksema H, Mizsak SA, Baczynskyj L. The chemistry of rubradirin. III. The rubradiric acids and the structure of rubradirin. J Antibiot (Tokyo). 1979 Jul;32(7):773-6. PubMed PMID: 541275.

15: Hoeksema H, Chidester C, Mizsak SA, Baczynskyj L. The chemistry of the rubradirins. I. The structures of rubransarols A and B. J Antibiot (Tokyo). 1978 Oct;31(10):1067-9. PubMed PMID: 711615.

16: Lamichhane J, Liou K, Lee HC, Kim CG, Sohng JK. Functional characterization of ketoreductase (rubN6) and aminotransferase (rubN4) genes in the gene cluster of Streptomyces achromogenes var. rubradiris. Biotechnol Lett. 2006 Apr;28(8):545-53. PubMed PMID: 16614891.

17: Reusser F. Rubradirin, an inhibitor of ribosomal polypeptide biosynthesis. Biochemistry. 1973 Mar 13;12(6):1136-42. PubMed PMID: 4569770.

18: Khatri I, Subramanian S, Mayilraj S. Genome sequencing and annotation of Amycolatopsis azurea DSM 43854(T). Genom Data. 2014 Mar 12;2:44-5. doi: 10.1016/j.gdata.2013.12.003. eCollection 2014 Dec. PubMed PMID: 26484067; PubMed Central PMCID: PMC4536004.

19: Hu Y, Al-Mestarihi A, Grimes CL, Kahne D, Bachmann BO. A unifying nitrososynthase involved in nitrosugar biosynthesis. J Am Chem Soc. 2008 Nov 26;130(47):15756-7. doi: 10.1021/ja8051415. PubMed PMID: 18983146; PubMed Central PMCID: PMC2661260.

20: Parajuli N, Viet HT, Ishida K, Tong HT, Lee HC, Liou K, Sohng JK. Identification and characterization of the afsR homologue regulatory gene from Streptomyces peucetius ATCC 27952. Res Microbiol. 2005 Jun-Jul;156(5-6):707-12. Epub 2005 Apr 21. PubMed PMID: 15921897.