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N6-(delta 2-Isopentenyl)-adenine, also known as isopentenyl purine, 6- (gamma, gamma dimethylallylamine) purine, 6- (gamma, gamma dimethylallylamine) purine, or 2-IP, is an important compound with various biochemical and medical applications. CAS 2365-40-4, The molecular formula C10H13N5 is usually a white crystalline or crystalline powder, sometimes described as a white to off white powder with a sour taste. Difficult to dissolve in water, but under certain conditions (such as 1M HCl), solubility may increase, such as ≥ 10mg/mL in 1M HCl.
Insoluble in ethanol and ether in organic solvents, soluble in acid and alkali salt solutions. It has multiple uses and broad application prospects. In terms of plant growth regulation, it can promote cell division and differentiation, delay plant tissue aging, promote organ formation, and promote flower bud differentiation; In the fields of biochemistry and medical clinical research, it can be used as a biochemical reagent, organic synthesis intermediate, and metal chelating agent; In other fields, it can also be used as a cosmetic additive, a drug for treating liver and heart diseases, and an additive for amino acid infusion. However, when using 2-IP, attention should be paid to concentration control, usage period, environmental conditions, and safety to ensure its optimal regulatory effect and application value.
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Chemical Formula |
C8H15NO6 |
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Exact Mass |
221.09 |
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Molecular Weight |
221.21 |
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m/z |
221.09 (100.0%), 222.09 (8.7%), 223.09 (1.2%) |
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Elemental Analysis |
C, 43.44; H, 6.84; N, 6.33; O, 43.40 |
The synthesis methods of N6-(delta 2-Isopentenyl)-adenine (6- (gamma, gamma dimethylallylamino) purine) may include the following:
1. Enzymatic conversion method
Method 1:
Using L-aspartic acid as raw material, L-alanine is produced through decarboxylation reaction catalyzed by aspartic acid - β - decarboxylase.
L-aspartic acid is produced by fermentation of fumaric acid with Escherichia coli ATCCll030 and Pseudomonas NX-1 cells.
Aspartate - β - decarboxylase solution was obtained through strain screening and two-stage strain cultivation.
The conversion solution is processed through steps such as enzyme killing, decolorization, filtration, crystallization, centrifugation, washing, and drying to obtain the finished product.
Method 2 (immobilized enzyme method):
Using fumaric acid as raw material, it is first converted into L-aspartic acid with NH3 under the action of aspartic acid enzyme.
L-aspartic acid undergoes decarboxylation under the action of immobilized Pseudomonas aeruginosa β - decarboxylase to obtain L-alanine.
2. Chemical synthesis method
Chemical synthesis is carried out using Strecker method or Bucherer method, followed by optical separation to obtain L-alanine boutique. However, it should be noted that this method does not directly synthesize 2-IP, but rather synthesizes its possible raw materials or intermediates.
3. One-step synthesis
A patent introduces a one-step method for synthesizing isopentenyl adenine or its derivatives, which involves reacting specific compounds in the presence of alkaline reagents to prepare the target compound. This method can effectively reduce production costs, improve product yield, and obtain high-purity products without complex post-processing steps.
4. Other possible synthetic pathways
Considering that 2-IP is a plant growth regulator, its synthesis pathway may involve other biochemical or chemical methods. These pathways may include the use of microbial fermentation, chemical catalysis, or biotransformation to convert specific precursor compounds into 2-IP.
In summary, the synthesis methods of 2-IP are diverse, including enzymatic conversion, chemical synthesis, and one-step synthesis. In practical applications, suitable synthesis methods can be selected based on specific needs and conditions. Meanwhile, with the continuous development of science and technology, new synthesis methods and pathways may also emerge.
N6-(delta 2-Isopentenyl)-adenine is a hormone organic compound with multiple uses, especially playing an important role in plant growth regulation, biochemical and medical clinical research, organic synthesis, and other fields.
Plant growth regulators
2-IP has significant effects on plant growth regulation, mainly by promoting cell division and differentiation, delaying plant tissue aging, promoting organ formation, and promoting flower bud differentiation.
(1) Promote cell division and differentiation
2-IP can stimulate plant cell division, promote cell proliferation and differentiation. This characteristic makes it play an important role in plant growth and development, especially during the rapid growth stage of plant tissues, such as root tips, stem tips, and other growth points.
(2) Delaying plant tissue aging
By regulating the metabolic processes in plants, 2-IP can delay the aging of plant tissues, thereby prolonging the growth period of plants and improving their yield and quality.
This is of great significance for improving the stress resistance, disease resistance, and extending the storage period of crops.
(3) Promote organ formation
2-IP can promote the formation of plant organs such as roots, stems, leaves, flowers, and fruits. By regulating hormone levels in plants, it can affect the growth and development of plant organs, making them more robust and yielding.
(4) Promote flower bud differentiation
During the reproductive growth stage of plants, 2-IP can promote flower bud differentiation, increase flowering and fruiting rates of plants.
This is of great significance for improving the yield and quality of crops, especially in economic crops such as fruit trees and flowers.
(5) Inducing parthenocarpy
2-IP can also induce parthenocarpy in plants, which means fruit can be formed without fertilization. This characteristic is of great significance in fruit tree cultivation, as it can increase fruit yield and quality, while reducing seed formation and lowering seed management costs.
(6) Improve fruit set rate
By promoting flower bud differentiation and increasing fertilization rate, 2-IP can significantly improve the fruit setting rate of plants. This is of great significance for improving the yield and quality of fruit trees, especially in areas with dense fruit tree planting and high management costs.
Specific application examples
Corn: 2-IP can promote maize jointing, tasseling, flowering, and maturation earlier, and increase the position and length of the ear nodes, reduce the number of bald tips, increase the number of grains, and increase the thousand grain weight.
Watermelon: spray with 600 times of liquid medicine every 10 days for three times, which can make the watermelon vine vigorous in the early stage, unfailing in the middle and late stages, and increase the sugar content and yield.
Chinese cabbage: Spraying 1ppm medicinal solution three times, with an interval of ten days, can achieve increased yield.
Eggplant: Spraying 1ppm solution six times, with an interval of ten days, can achieve flower and fruit preservation and increase yield.
Tomatoes: Spraying 1ppm solution five times, with an interval of ten days, can achieve flower and fruit preservation, and increase yield.
Tea leaves: Spray 1ppm solution three times, with a seven day interval, to increase caffeine and tea polyphenols and improve quality.
Rice: Spraying 1ppm solution three times with an interval of 7-10 days can achieve increased yield.
Citrus: During the flowering period and the late stage of the first physiological fruit drop, spraying with a concentration of 1ppm of the medicine solution evenly can significantly increase the fruit setting rate; During the fruit coloring period (late July to late September), evenly spraying with a concentration of 1ppm of medicinal solution can make the fruit appear orange red in color and have a high sugar content.
Biochemical and Medical Clinical Research
2-IP also has important application value in the fields of biochemistry and medical clinical research. It can be used as a biochemical reagent, organic synthesis intermediate, and metal chelating agent, providing support for medical research and clinical diagnosis.
(1) Biochemical reagents
2-IP can be used as a biochemical reagent for monitoring and analyzing biochemical reactions. By interacting with other biomolecules, it can reveal metabolic processes and signaling mechanisms within the organism, providing important clues for medical research.
(2) Organic synthesis intermediates
In the field of organic synthesis, 2-IP can serve as an intermediate for the synthesis of other compounds.
By modifying and altering its chemical structure, compounds with specific biological activities can be prepared, providing important raw materials for drug development and biomaterial preparation.
(3) Metal chelating agent
2-IP can also form complexes with metal ions, which have important application value in medical research and clinical diagnosis. By binding with metal ions, it can alter the biological activity and toxicity of metal ions, providing support for their detection and detoxification.
Other uses
In addition to the above-mentioned application fields, 2-IP also has various other uses.
(1) Cosmetics
2-IP can be used as an additive in cosmetics, with moisturizing, antioxidant, and anti-aging effects. By regulating the metabolic processes of skin cells, it can improve the texture and radiance of the skin, making it healthier and more youthful.
(2) Liver and heart disease treatment
Research has shown that 2-IP also has certain potential applications in the treatment of liver disease and heart disease.
By regulating the metabolic processes of liver and heart cells, it can reduce the degree of damage to the liver and heart, promote the repair and regeneration of damaged cells.
(3)Amino Acid Infusion Solution
N6-(delta 2-Isopentenyl)-adenine can also be used as an additive in aminoacid infusion solutions,providingessential nutrients for the human body.
By supplementing amino acids andother nutrients,it can improve thenutritional status of the human bodyand enhance immunity.
Discovery Background (1950s–1960s)
The discovery of 2iP originated from the research boom of cytokinins. In 1955, Miller and Skoog first isolated kinetin, a synthetic cytokinin, from herring sperm DNA. In 1963, Letham identified zeatin, the first naturally occurring cytokinin, from maize, which promoted the search for natural purine cytokinins.
First Isolation and Identification (Late 1960s)
In the late 1960s, researchers isolated a highly active cytokinin from the culture filtrate of the plant pathogen Corynebacterium fascians and various plant tissues. Analyzed by mass spectrometry, infrared spectroscopy and other methods, it was identified as an adenine substituted with an isopentenyl group at the N⁶-position, and named N⁶-(Δ²-isopentenyl)-adenine (2iP).
Confirmation of Biological Significance (1970s)
In the 1970s, it was confirmed that 2iP is a rare modified base in the anticodon loop of tRNA and participates in translational regulation. As a natural plant hormone, it strongly promotes cell division and shoot differentiation, becoming a key reagent in tissue culture. Its discovery improved the cytokinin family and revealed the structural diversity of natural hormones.
The product is a versatile molecule with profound implications for plant science, microbiology, and human health. Its ability to modulate cell division, stress responses, and metabolic pathways underscores its value in sustainable agriculture and biotechnology. Future research should focus on optimizing production costs, exploring novel delivery mechanisms, and unraveling its mechanisms of action in non-plant systems. As global challenges like climate change and food security intensify, 2IP stands out as a promising tool for enhancing crop productivity and ecological resilience.
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