28542-78-1

Basic information

• Product Name: TRANS-ZEATIN RIBOSIDE
• Synonyms: 6-[(E)-4-HYDROXY-3-METHYLBUT-2-ENYLAMINO]-9-B-D-RIBOFURANOSYLPURINE;6-[(E)-4-HYDROXY-3-METHYLBUT-2-ENYLAMINO]-9-BETA-D-RIBOFURANOSYLPURINE;9-(BETA-D-RIBOFURANOSYL)-TRANS-ZEATIN;ZEATIN RIBOSIDE;ZEATIN RIBOSIDE TRANS ISOMER;zeatin riboside mixed isomers;N6-(4-Hydroxy-3-methylbut-2-enyl)adenosine;ZEATIN RIBOSIDE mixed isomers (E/Z)
• CAS NO: 28542-78-1
• Molecular Formula: C15H21N5O5
• Molecular Weight: 351.36
• Product Categories: Miscellaneous Natural Products;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 28542-78-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 176-179 °C
• Boiling Point: 731.8°Cat760mmHg
• Flash Point: 396.4°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 1.77E-22mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: −20°C
• Solubility: acetic acid: 50 mg/mL, clear, colorless
• CAS DataBase Reference: TRANS-ZEATIN RIBOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-ZEATIN RIBOSIDE(28542-78-1)
• EPA Substance Registry System: TRANS-ZEATIN RIBOSIDE(28542-78-1)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 28542-78-1(Hazardous Substances Data)

Usage

Description

TRANS-ZEATIN RIBOSIDE, also known as an N-glycosylzeatin, is a chemical compound derived from zeatin, a plant growth regulator. It is characterized by the replacement of the hydrogen attached to the nitrogen at position 9 of the adenine moiety with a beta-D-ribofuranosyl group. This modification gives TRANS-ZEATIN RIBOSIDE unique properties that make it valuable for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
TRANS-ZEATIN RIBOSIDE is used as a biological study agent for investigating the putative role of adenosine A3 receptor in the anti-proliferative action of N6-(2-isopentyl)adenosine. This application is significant in understanding the underlying mechanisms of certain biological processes and can potentially lead to the development of new therapeutic strategies.
Used in Agricultural Industry:
As a derivative of zeatin, a well-known plant growth regulator, TRANS-ZEATIN RIBOSIDE can be used as a growth enhancer in the agricultural industry. Its application can promote plant growth, increase crop yield, and improve overall plant health by modulating various physiological processes.
Used in Research and Development:
TRANS-ZEATIN RIBOSIDE can be utilized as a research tool in the development of new bioactive compounds and pharmaceuticals. Its unique structure and properties make it a valuable candidate for studying various biological pathways and mechanisms, which can contribute to the advancement of scientific knowledge and the creation of novel therapeutic agents.

InChI:InChI=1/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2+/t9-,11-,12-,15-/m1/s1

Upstream product

• 13114-27-7 2-methyl-4-(7⁽⁹⁾H-purin-6-ylamino)-but-2-en-1-ol 
• 7724-76-7 6-N-(3,3-dimethylallyl)adenosine 
• 5451-40-1 2,6 dichloropurine 
• 6025-53-2 6-((E)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine 

Downstream Products

• 6025-53-2 6-((Z)-4-hydroxy-3-methylbut-2-enylamino)-9-β-D-ribofuranosylpurine 

Relevant articles and documents

Peroxide-shunt substrate-specificity for the Salmonella typhimurium O 2-dependent tRNA modifying monooxygenase (MiaE)

Post-transcriptional modifications of tRNA are made to structurally diversify tRNA. These modifications alter noncovalent interactions within the ribosomal machinery, resulting in phenotypic changes related to cell metabolism, growth, and virulence. MiaE is a carboxylate bridged, nonheme diiron monooxygenase, which catalyzes the O2-dependent hydroxylation of a hypermodified-tRNA nucleoside at position 37 (2-methylthio-N6- isopentenyl-adenosine(37)-tRNA) [designated ms2i6A 37]. In this work, recombinant MiaE was cloned from Salmonella typhimurium, purified to homogeneity, and characterized by UV-visible and dual-mode X-band EPR spectroscopy for comparison to other nonheme diiron enzymes. Additionally, three nucleoside substrate-surrogates (i6A, Cl2i6A, and ms2i6A) and their corresponding hydroxylated products (io6A, Cl2io 6A, and ms2io6A) were synthesized to investigate the chemo- and stereospecificity of this enzyme. In the absence of the native electron transport chain, the peroxide-shunt was utilized to monitor the rate of substrate hydroxylation. Remarkably, regardless of the substrate (i6A, Cl2i6A, and ms2i6A) used in peroxide-shunt assays, hydroxylation of the terminal isopentenyl-C4-position was observed with >97% E-stereoselectivity. No other nonspecific hydroxylation products were observed in enzymatic assays. Steady-state kinetic experiments also demonstrate that the initial rate of MiaE hydroxylation is highly influenced by the substituent at the C2-position of the nucleoside base (v0/[E] for ms2i6A > i 6A > Cl2i6A). Indeed, the >3-fold rate enhancement exhibited by MiaE for the hydroxylation of the free ms 2i6A nucleoside relative to i6A is consistent with previous whole cell assays reporting the ms2io6A and io6A product distribution within native tRNA-substrates. This observation suggests that the nucleoside C2-substituent is a key point of interaction regulating MiaE substrate specificity.