20268-93-3

Basic information

• Product Name: N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate
• Synonyms: N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate;IPAMP;Isopentenyladenine 9-riboside monophosphate;Isopentenyladenosine monophosphate;N-(3-Methyl-2-butenyl)-5'-adenylic acid;N-(3-Methyl-2-butenyl)adenosine 5'-phosphoric acid;N-Isopentenyladenosine 5'-phosphoric acid;N6-ISOPENTENYLADENOSINE-5'-MONOPHOSPHATE SODIUM SALT (iPMP)
• CAS NO: 20268-93-3
• Molecular Formula: C₁₅H₂₂N₅O₇P
• Molecular Weight: 415.34
• Mol File: 20268-93-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate(20268-93-3)
• EPA Substance Registry System: N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate(20268-93-3)

Safety Data

• Hazardous Substances Data: 20268-93-3(Hazardous Substances Data)

Usage

Description

N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate, also known as N6-Isopentenyladenosine-5'-monophosphate, is a modified nucleotide derived from adenosine 5'-monophosphate (AMP). It features a dimethylallyl group attached to the N6 position, which is significant for its biological functions and stability. N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate is a key molecule in various cellular processes and has been found to play a role in the regulation of gene expression and cellular signaling.

Uses

Used in Biological Studies:
N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate is used as a research tool for studying the effects of light on growth and endogenous hormones in microalgae. Its stable sodium salt form makes it more suitable for experimental procedures compared to its free base counterpart.
Used in Pharmaceutical Industry:
N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate is used as an active pharmaceutical ingredient for the development of drugs targeting various diseases. Its role in cellular signaling and gene regulation makes it a potential candidate for therapeutic applications.
Used in Agricultural Industry:
In the agricultural industry, N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate can be used to enhance the growth and productivity of microalgae, which are essential for various applications, including biofuel production, animal feed, and the production of high-value compounds.
Used in Chemical Research:
N(6)-(delta(2)-isopentenyl)adenosine 5'-monophosphate is used as a chemical intermediate for the synthesis of other nucleotide derivatives and related compounds. Its unique structure and properties make it a valuable building block in the development of novel chemical entities with potential applications in various fields.

Upstream product

• 358-72-5 dimethylallyl diphosphate 
• 61-19-8 5'-adenosine monophosphate 
• 13822-06-5 3,3-dimethylallylamine 
• 128184-91-8 6-chloro-9-(2',3'-O-methoxymethyliden-β-D-ribofuranosyl) purine 
• 128184-96-3 6-<3-methyl-2-butenylamino>-9-(2',3'-O-methoxymethylidene-β-D-ribofuranosyl) purine 
• 2004-06-0 6-Chloropurine riboside 

Downstream Products

• 7724-76-7 6-N-(2-isopentenyl)adenosine 

Relevant articles and documents

Molecular cloning, expression, and characterization of adenylate isopentenyltransferase from hop (Humulus lupulus L.)

A cDNA encoding adenylate isopentenyltransferase was cloned and sequenced from Humulus lupulus L. The corresponding recombinant enzyme expressed in Escherichia coli catalyzed isopentenyl transfer reaction from DMAPP to the N6 amino group of AMP, ADP and ATP, respectively. Site-directed mutagenesis of a conserved Asp62 resulted in complete loss of enzyme activity. A cDNA encoding adenylate isopentenyltransferase (AIPT) was cloned and sequenced from cones of hop (Humulus lupulus L.) by RT-PCR using oligonucleotide primers based on the conserved sequences of Arabidopsis thaliana AIPT isozymes (AtIPT1, AtIPT3, AtIPT4, AtIPT5, AtIPT6, AtIPT7 and AtIPT8). A full-length cDNA contained a 990-bp open reading frame encoding a molecular mass of 36,603 Da protein with 329 amino acids. Further, DNA sequencing of genomic DNA revealed absence of introns in the frame. On Southern blot analysis, a single AIPT gene was detected in H. lupulus, while RT-PCR analyses demonstrated that the gene was equally expressed in almost all tissues in the plant including roots, stems, leaves and cones. The deduced amino acid sequence shares 38-51% identity to those of A. thaliana AtIPTs. A recombinant enzyme expressed in Escherichia coli catalyzed isopentenyl transfer reaction from dimethylallyldiphosphate (DMAPP) to the N6 amino group of adenosine monophosphate (AMP), adenosine diphosphate (ADP) and adenosine triphosphate (ATP), respectively. In contrast, other nucleotides; guanosine monophosphate (GMP), inosine monophosphate (IMP), cytosine monophosphate (CMP), uridine monophosphate (UMP), were not accepted as a substrate. Interestingly, steady-state kinetic analyses revealed that the isopentenylation of ADP and ATP were more efficient than that of AMP as previously reported for A. thaliana AtIPT4. Finally, H. lupulus AIPT contains the putative ATP/GTP binding motif at the N-terminal as in the case of other known isopentenyltransferases. Site-directed mutagenesis of a conserved Asp62, located right after the ATP/GTP binding motif, with Ala resulted in complete loss of enzyme activity.

THE SYNTHESIS OF CYTOKININ PHOSPHATES

The bifunctional phosphorylating reagent N-morpholino O,O-bisphosphate was used for the preparation of ribosyl zeatin 5'-phosphate 1b and N6-(Δ2-Isopentenyl)adenosine 5'-phosphate 2b, whereas the monofunctional phosphitylating reagent 2-chloro-4H-1,3,2-benzodioxaphosphorin-4-one was used for the preparation of ribosyl zeatin allylic phosphate 1d and ribosyl zeatin diphosphate 1c.