Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-2-(methylthio)-, (E)-

Base Information

• Chemical Name: Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-2-(methylthio)-, (E)-
• CAS No.: 53274-45-6
• Molecular Formula: C16H23N5O5S
• Molecular Weight: 397.44900
• Mol file: 53274-45-6.mol

Synonyms:2-METHYLTHIO-TRANS-ZEATIN RIBOSIDE;

Chemical Property of Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-2-(methylthio)-, (E)-

Chemical Property:

• Melting Point: 80 - 130 °C
• PSA: 171.08000
• LogP: -0.41680

Purity/Quality:

2-Methylthio-trans-zeatinRiboside(2MeStZR) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Methylthio-trans-zeatin Riboside can be used in biological study for steady-state kinetics and spectroscopic characterization of enzyme-tRNA interactions for non-heme diiron tRNA-monooxygenase MiaE.

Technology Process of Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-2-(methylthio)-, (E)-

There total 8 articles about Adenosine, N-(4-hydroxy-3-methyl-2-butenyl)-2-(methylthio)-, (E)- 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:

→ 6-(4-Hydroxy-3-methyl-cis-2-butenylamino)-2-methylthio-9α-D-ribofuranosylpurin (26190-61-4,52049-48-6,52049-49-7,53274-45-6)

Guidance literature:

d.Ribofuranosylpurin 7b durch Rk. mit CH3SH und N2;

DOI:10.1016/S0031-9422(00)91263-9

Reference yield:

(3-methyl-2-butenyl)amine hydrochloride (26728-58-5) → 2-Methylthio-trans-ribosylzeatin (53274-45-6)

Guidance literature:

Multi-step reaction with 4 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

4: Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide / dimethyl sulfoxide / 1 h / 27 °C / pH 8 / Enzymatic reaction

With methanol; trimethylsilyl trifluoromethanesulfonate; Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide; sodium methylate; potassium carbonate; In dimethyl sulfoxide; acetonitrile; butan-1-ol; 2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/bi4000832

Reference yield:

C22H29N5O7S → 2-Methylthio-trans-ribosylzeatin (53274-45-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide / dimethyl sulfoxide / 1 h / 27 °C / pH 8 / Enzymatic reaction

With methanol; Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase; dihydrogen peroxide; sodium methylate; In dimethyl sulfoxide;

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

Refernces

• 1、 Corder, Andra L.,Subedi, Bishnu P.,Zhang, Siai,Dark, Amanda M.,Foss Jr., Frank W.,Pierce, Brad S.. "Peroxide-shunt substrate-specificity for the Salmonella typhimurium O 2-dependent tRNA modifying monooxygenase (MiaE)". . p. 6182 - 6196. Retrieved 2013/10/01.