Jasmonic acid carboxyl

Subsequently, JA can be metabolized in the cytoplasm by at least seven different reactions. Well-characterized reactions include methyla-tion to methyl-jasmonate (MeJA) by S-adenosyl-L-methionine jasmonic acid carboxyl methyl transferase (JMT), conjugation to amino acids by JA amino acid synthase (JARl) or hydroxylation to 12-hydroxyjasmonic acid(12-OH-JA). OPDA, JA, MeJA and JA-Ile are active signalling molecules, whereas 12-OH-JA is thought to be a biologically inactive derivative (Wastemack, 2007). 

Fig, 1 Schematic representation of the octadecanoid pathway leading to jasmonic acid biosynthesis. 12-OH-JA, 12-hydroxy-jasmonic acid AOC, allene oxide cyclase AOS, allene oxide synthase JA, jasmonic acid JARl, enzyme responsible for the conjugation of JA with isoleucine (JA-Ile) JMT, 5 -adenosyl-L-methionine jasmonic acid carboxyl methyl transferase LA, a-linolenic acid LOX, lipoxygenase MeJA, methyl jasmonate OPDA, 12-oxo-phytodienoic acid OPR3, OPDA reductaseS PL, phospholipase... 

Fig. 5 Branches of the lipoxygenase (LOX) pathway leading to the biosynthesis of volatile compounds. The allene oxide synthase (AOS) branch leading to methyl jasmonate is shown on the blue background hydroperoxyde lyase (HPL) branches, giving rise to C6- and C9-volatiles, are shown on the green background. AAT, alcohol acyltransferase ADH, alcohol dehydrogenase AI, alkene iso-merase JMT, jasmonic acid carboxyl methyltransferase...

Seo, H.S., et al. (2001) Jasmonic acid carboxyl methyltransferase A key enzyme for jas-monate-regulated plant responses. Proc. Natl. Acad. Sci. USA 98,4788 793... 

Song, M.S., et al. (2005) Isolation and characterization of a jasmonic acid carboxyl methyltransferase gene from hot pepper (Capsicum annuum L.). J. Plant Biol. 48,292-297... 

Small molecule carboxylates are an important class of compounds that plants produce to attract pollinators,44 defend against herbivory,45 7 regulate the cell cycle,48,49 and induce defense responses.50 5 Often these compounds are esterified and volatilized. Plants utilize the emission of volatile esters as chemoattractants and signaling molecules. Classes of volatile compounds include the salicylates and jasmonates, which are ubiquitously distributed in the plant kingdom. Jasmonic acid, salicylic acid, and their methyl ester derivatives, are intimately involved in cell regulation and help control such developmental processes as seed germination, flower development, fruit development, and senescence.14,17,53... 

Knofel et al. [92] prepared and used a BSA conjugate from racemic jasmonic acid, linked via amide bond to the carboxyl function. Serum arising from this conjugate was used to develop a radioimmunoassay. The antibodies required methylation of jasmonic... 

The product of hydroperoxide cyclase, 12-oxo-PDA, is a key intermediate in the biosynthesis of jasmonic acid (17) (Fig. 2). First, the ring double bond of 12-oxo-PDA is reduced by NADPH in the presence of 12-oxo-PDA reductase (18). Then, after three cycles of 8-oxidation of the carboxyl side chain, jasmonic acid is formed. 

The first of these is impressive for the high yield and the lack of interference by the carboxylic acid group. The second is important because the product is the perfumery compound a s-jasmone found naturally in jasmine flowers, and is formed in good yield with no change in the position or geometry of the Z double bond. 

Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester. See Methyl jasmonate Cyclopentaneacetic acid, 3-oxo-2-pentyl-, methyl ester. See Methyidihydrojasmonate Cyclopentane, butyl-. See Butylcyclopentane Cyclopentane carboxylic acid CAS 3400-45-1 EINECS/ELINCS 222-269-5 Classification Nonaromatic carboxylic acid Empirical C6H10O2 Formula C5H9CO2H... 

Methyl-2H-azirine-2-carboxylic acid, 979 Methyl jasmonate (MeJA/MeJa), 92, 94, 98, 106, 107, 109, 1690, 1696-1699, 1703, 1706,1707,2784,2954,2956, 2958, 4045 Methylliberine, 956 Methylmercaptan, 2899 2-Methyl-mercapto-propylamine (MMPA), 2885... 

This methodology was also applied to the crossed Claisen reaction between carboxylic acids and methyl hexanoate. The carboxylic acids are initially converted to mixed anhydrides by reacting their in situ formed sodium carboxylates with chlorofor-mates these intermediates then react with NMI as shown previously to form electrophilic acyl ammonium species (eq 46). This strategy was applied to the synthesis of natural perfumes such as (/ )-muscone and cw-jasmone. ... 

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