ms2i6A

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

MedKoo CAT#: 565796

CAS#: 20859-00-1

Description: ms2i6A is a mitochondrial tRNA-specific modification, which regulates efficient mitochondrial translation and energy metabolism in mammals.


Chemical Structure

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ms2i6A
CAS# 20859-00-1

Theoretical Analysis

MedKoo Cat#: 565796
Name: ms2i6A
CAS#: 20859-00-1
Chemical Formula: C16H23N5O4S
Exact Mass: 381.1471
Molecular Weight: 381.45
Elemental Analysis: C, 50.38; H, 6.08; N, 18.36; O, 16.78; S, 8.40

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: ms2i6A; ms2i6 2 6; ms2i6-2-6

IUPAC/Chemical Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((3-methylbut-2-en-1-yl)amino)-2-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

InChi Key: VZQXUWKZDSEQRR-SDBHATRESA-N

InChi Code: InChI=1S/C16H23N5O4S/c1-8(2)4-5-17-13-10-14(20-16(19-13)26-3)21(7-18-10)15-12(24)11(23)9(6-22)25-15/h4,7,9,11-12,15,22-24H,5-6H2,1-3H3,(H,17,19,20)/t9-,11-,12-,15-/m1/s1

SMILES Code: C/C(C)=C\CNC1=C(N=CN2[C@@]3([H])[C@@](O)([H])[C@@](O)([H])[C@@](O3)([H])CO)C2=NC(SC)=N1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 381.45 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

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1: Fakruddin M, Wei FY, Emura S, Matsuda S, Yasukawa T, Kang D, Tomizawa K. Cdk5rap1-mediated 2-methylthio-N6-isopentenyladenosine modification is absent from nuclear-derived RNA species. Nucleic Acids Res. 2017 Nov 16;45(20):11954-11961. doi: 10.1093/nar/gkx819. PubMed PMID: 28981754; PubMed Central PMCID: PMC5714233.

2: Díaz I, Ehrenberg M. ms2i6A deficiency enhances proofreading in translation. J Mol Biol. 1991 Dec 20;222(4):1161-71. PubMed PMID: 1762149.

3: Connolly DM, Winkler ME. Structure of Escherichia coli K-12 miaA and characterization of the mutator phenotype caused by miaA insertion mutations. J Bacteriol. 1991 Mar;173(5):1711-21. PubMed PMID: 1999389; PubMed Central PMCID: PMC207322.

4: Vacher J, Grosjean H, Houssier C, Buckingham RH. The effect of point mutations affecting Escherichia coli tryptophan tRNA on anticodon-anticodon interactions and on UGA suppression. J Mol Biol. 1984 Aug 5;177(2):329-42. PubMed PMID: 6379198.

5: Wilson RK, Roe BA. Presence of the hypermodified nucleotide N6-(delta 2-isopentenyl)-2-methylthioadenosine prevents codon misreading by Escherichia coli phenylalanyl-transfer RNA. Proc Natl Acad Sci U S A. 1989 Jan;86(2):409-13. PubMed PMID: 2643111; PubMed Central PMCID: PMC286479.

6: McLennan BD, Buck M, Humphreys J, Griffiths E. Iron-related modification of bacterial transfer RNA. Nucleic Acids Res. 1981 Jun 11;9(11):2629-40. PubMed PMID: 6792594; PubMed Central PMCID: PMC326877.

7: Buck M, Ames BN. A modified nucleotide in tRNA as a possible regulator of aerobiosis: synthesis of cis-2-methyl-thioribosylzeatin in the tRNA of Salmonella. Cell. 1984 Feb;36(2):523-31. PubMed PMID: 6362893.

8: Persson BC, Björk GR. Isolation of the gene (miaE) encoding the hydroxylase involved in the synthesis of 2-methylthio-cis-ribozeatin in tRNA of Salmonella typhimurium and characterization of mutants. J Bacteriol. 1993 Dec;175(24):7776-85. PubMed PMID: 8253666; PubMed Central PMCID: PMC206952.

9: Durand JM, Björk GR, Kuwae A, Yoshikawa M, Sasakawa C. The modified nucleoside 2-methylthio-N6-isopentenyladenosine in tRNA of Shigella flexneri is required for expression of virulence genes. J Bacteriol. 1997 Sep;179(18):5777-82. PubMed PMID: 9294434; PubMed Central PMCID: PMC179466.

10: Persson BC, Olafsson O, Lundgren HK, Hederstedt L, Björk GR. The ms2io6A37 modification of tRNA in Salmonella typhimurium regulates growth on citric acid cycle intermediates. J Bacteriol. 1998 Jun;180(12):3144-51. PubMed PMID: 9620964; PubMed Central PMCID: PMC107815.

11: Pierrel F, Hernandez HL, Johnson MK, Fontecave M, Atta M. MiaB protein from Thermotoga maritima. Characterization of an extremely thermophilic tRNA-methylthiotransferase. J Biol Chem. 2003 Aug 8;278(32):29515-24. Epub 2003 May 24. PubMed PMID: 12766153.

12: Janzer JJ, Raney JP, McLennan BD. The transfer RNA of certain Enterobacteriacae contain 2-methylthiozeatin riboside (ms2io6A) an isopentenyl adenosine derivative. Nucleic Acids Res. 1982 Sep 25;10(18):5663-72. PubMed PMID: 6815620; PubMed Central PMCID: PMC320914.

13: Mangroo D, Wu XQ, RajBhandary UL. Escherichia coli initiator tRNA: structure-function relationships and interactions with the translational machinery. Biochem Cell Biol. 1995 Nov-Dec;73(11-12):1023-31. Review. PubMed PMID: 8722017.

14: Connolly DM, Winkler ME. Genetic and physiological relationships among the miaA gene, 2-methylthio-N6-(delta 2-isopentenyl)-adenosine tRNA modification, and spontaneous mutagenesis in Escherichia coli K-12. J Bacteriol. 1989 Jun;171(6):3233-46. PubMed PMID: 2656644; PubMed Central PMCID: PMC210042.

15: Caillet J, Droogmans L. Molecular cloning of the Escherichia coli miaA gene involved in the formation of delta 2-isopentenyl adenosine in tRNA. J Bacteriol. 1988 Sep;170(9):4147-52. PubMed PMID: 3045085; PubMed Central PMCID: PMC211421.

16: Jayabaskaran C. Immunospecific binding of tRNA precursors containing N6-(delta 2-isopentenyl) adenosine. Biochem Int. 1984 Feb;8(2):257-64. PubMed PMID: 6566571.

17: Wang H, Wei L, Li C, Zhou J, Li Z. CDK5RAP1 deficiency induces cell cycle arrest and apoptosis in human breast cancer cell line by the ROS/JNK signaling pathway. Oncol Rep. 2015 Mar;33(3):1089-96. doi: 10.3892/or.2015.3736. Epub 2015 Jan 20. PubMed PMID: 25607831.

18: Bouadloun F, Srichaiyo T, Isaksson LA, Björk GR. Influence of modification next to the anticodon in tRNA on codon context sensitivity of translational suppression and accuracy. J Bacteriol. 1986 Jun;166(3):1022-7. PubMed PMID: 3086285; PubMed Central PMCID: PMC215227.

19: Mangroo D, Limbach PA, McCloskey JA, RajBhandary UL. An anticodon sequence mutant of Escherichia coli initiator tRNA: possible importance of a newly acquired base modification next to the anticodon on its activity in initiation. J Bacteriol. 1995 May;177(10):2858-62. PubMed PMID: 7751297; PubMed Central PMCID: PMC176959.

20: Buck M, Griffiths E. Iron mediated methylthiolation of tRNA as a regulator of operon expression in Escherichia coli. Nucleic Acids Res. 1982 Apr 24;10(8):2609-24. PubMed PMID: 7043398; PubMed Central PMCID: PMC320637.