19427-32-8

Usage

Uses

Used in Plant Growth Regulation:
Gibberellin A(24) is used as a plant growth regulator to promote growth and development in various plant species. It helps in stimulating processes such as germination, stem elongation, and flowering, leading to improved crop yields and quality.
Used in Seed Germination:
Gibberellin A(24) is used as a seed germination agent to enhance the germination rate and speed up the process in various plant species. It helps overcome dormancy and improve the overall success of germination.
Used in Fruit Ripening:
Gibberellin A(24) is used as a fruit ripening agent to promote the ripening process in certain fruits, such as tomatoes and bananas. It helps in the development of color, texture, and flavor, making the fruits more appealing and suitable for consumption.
Used in Plant Tissue Culture:
Gibberellin A(24) is used as a growth factor in plant tissue culture applications, where it helps in the growth and development of plantlets from explants. It plays a vital role in the successful establishment of in vitro plant cultures for various purposes, including breeding, propagation, and genetic research.

InChI:InChI=1/C20H26O5/c1-11-8-20-9-12(11)4-5-13(20)19(10-21)7-3-6-18(2,17(24)25)15(19)14(20)16(22)23/h10,12-15H,1,3-9H2,2H3,(H,22,23)(H,24,25)/t12-,13+,14-,15-,18-,19-,20+/m1/s1

Upstream product

• 132842-63-8 (1R,4bR,7R,9aR,10S,10aS)-10-(methoxycarbonyl)-1-methyl-8-methylene-2,3,4b,5,6,7,8,9,10,10a-decahydro-1H-7,9a-methanobenzo[a]azulene-1-carboxylic acid 
• 91298-28-1 methyl (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-1-methyl-8-methylene-2,7-bis((methylsulfonyl)oxy)-13-oxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate 
• 1164-45-0 gibberellin A₁₂ 

Downstream Products

• 28535-69-5 gibberellin A₂₅ 

Relevant academic research and scientific papers

Syntheses of Gibberellins A15 and A24, the Key Metabolites in Gibberellin Biosynthesis

Gibberellins (GAs) are essential phytohormones involved in numerous aspects of plant growth and development. Notably, the biochemistry and genetics of GA biosynthesis, which is associated with their endogenous regulation, have been largely resolved; however, a crucial unsolved question remains: the precise mechanism of the stepwise oxidation and subsequent removal of C-20 from C20 precursors, leading to bioactive C19 gibberellins, is still unresolved. To satisfy numerous requests from biologists, practical preparations of certain GAs that were isolated in miniscule quantities are highly demanded. Herein, we report the first practical syntheses of GA15 and GA24, the key C20 metabolites in gibberellin biosynthesis, from commercially available GA3. The protocols are robust and offer the capacity to produce GA24 and GA15 under gram scales in high overall yields and thus aid in further biological and related studies.

Influence of electron transport proteins on the reactions catalyzed by Fusarium fujikuroi gibberellin monooxygenases

The multifunctional cytochrome P450 monooxygenases P450-1 and P450-2 from Fusarium fujikuroi catalyze the formation of GA14 and GA4, respectively, in the gibberellin (GA)-biosynthetic pathway. However, the activity of these enzymes is qualitatively and quantitatively different in mutants lacking the NADPH:cytochrome P450 oxidoreductase (CPR) compared to CPR-containing strains. 3β-Hydroxylation, a major P450-1 activity in wild-type strains, was strongly decreased in the mutants relative to oxidation at C-6 and C-7, while synthesis of C19-GAs as a result of oxidative cleavage of C-20 by P450-2 was almost absent whereas the C-20 alcohol, aldehyde and carboxylic acid derivatives accumulated. Interaction of the monooxygenases with alternative electron transport proteins could account for these different product distributions. In the absence of CPR, P450-1 activities were NADH-dependent, and stimulated by cytochrome b5 or by added FAD. These properties as well as the decreased efficiency of P450-1 and P450-2 in the mutants are consistent with the participation of cytochrome b5:NADH cytochrome b5 reductase as redox partner of the gibberellin monooxygenases in the absence of CPR. We provide evidence, from either incubations of GA12 (C-20 methyl) with cultures of the mutant suspended in [18O]H2O or maintained under an atmosphere of [18O]O2:N2 (20:80), that GA15 (C-20 alcohol) and GA24 (C-20 aldehyde) are formed directly from dioxygen and not from hydrolysis of covalently enzyme-bound intermediates. Thus these partially oxidized GAs correspond to intermediates of the sequential oxidation of C-20 catalyzed by P450-2.