2-Methylthio-N-6-isopentenyladenosine

Base Information

• Chemical Name: 2-Methylthio-N-6-isopentenyladenosine
• CAS No.: 20859-00-1
• Molecular Formula: C₁₆H₂₃N₅O₄S
• Molecular Weight: 381.456
• DSSTox Substance ID: DTXSID30943113
• Nikkaji Number: J38.557C
• Wikidata: Q27132248
• Metabolomics Workbench ID: 62467
• Mol file: 20859-00-1.mol

Synonyms:2-methyl-thio-N-6-isopentyladenosine;2-methylthio-N(6)-isopentenyladenosine;2-methylthio-N-6-isopentenyladenosine;2-MTIA;N(6)-(delta(2)-isopentenyl)-2-methylthioadenosine

Chemical Property of 2-Methylthio-N-6-isopentenyladenosine

Chemical Property:

• Vapor Pressure: 1.24E-21mmHg at 25°C
• Boiling Point: 718°Cat760mmHg
• Flash Point: 388°C
• PSA: 150.85000
• Density: 1.56g/cm³
• LogP: 0.61080
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 381.14707541
• Heavy Atom Count: 26
• Complexity: 509

Purity/Quality:

97% ^*data from raw suppliers

2-Methylthio-N6-isopentenyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCNC1=C2C(=NC(=N1)SC)N(C=N2)C3C(C(C(O3)CO)O)O)C
• Isomeric SMILES: CC(=CCNC1=C2C(=NC(=N1)SC)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)C
• Uses: 2-Methylthio-N6-isopentenyladenosine is located at position 37 in tRNAs that read codons starting with uridine. 2-Methylthio-N6-isopentenyladenosine in trpT(Su9) suppressor tRNA increase the efficiency of the tRNA by protecting it from ribosomal proofreading which is induced by codon context.

Technology Process of 2-Methylthio-N-6-isopentenyladenosine

There total 6 articles about 2-Methylthio-N-6-isopentenyladenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(3-methyl-2-butenyl)amine hydrochloride (26728-58-5) → 6-(3-Methyl-2-butenylamino)-2-methylthio-9-β-D-ribofuranosylpurin (20859-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / butan-1-ol / 5 h / 110 °C

2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 18 h / Reflux

3: sodium methylate; methanol / 6 h / 20 °C

With methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; In acetonitrile; butan-1-ol; 2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/bi4000832

Reference yield:

C22H29N5O7S → 6-(3-Methyl-2-butenylamino)-2-methylthio-9-β-D-ribofuranosylpurin (20859-00-1)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 6h;

DOI:10.1021/bi4000832

Reference yield:

2-methylthio-N-6-chloropurine (66191-23-9) → 6-(3-Methyl-2-butenylamino)-2-methylthio-9-β-D-ribofuranosylpurin (20859-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / butan-1-ol / 5 h / 110 °C

2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 18 h / Reflux

3: sodium methylate; methanol / 6 h / 20 °C

With methanol; trimethylsilyl trifluoromethanesulfonate; sodium methylate; potassium carbonate; In acetonitrile; butan-1-ol; 2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/bi4000832

upstream raw materials:

(3-methyl-2-butenyl)amine hydrochloride

2-methylthio-N-6-chloropurine

(3-methyl-but-2-enyl)-(2-methylsulfanyl-7⁽⁹⁾H-purin-6-yl)-amine

1,2,3,6-Tetrahydro-2-oxo-6-thioxo-7H-purine

Downstream raw materials:

2-Methylthio-trans-ribosylzeatin

Refernces

• 1、 Burrows,Armstrong,Skoog,Hecht,Boyle,Leonard,Occolowitz. "Cytokinin from soluble RNA of Escherichia coli: 6-(3-methyl-2-butenylamino)-2-methylthio-9-beta-D-ribofuranosylpurine.". . p. 691 - 693. Retrieved 1968.