Aminocyclopropane-l-carboxylic acid

Abbreviations ACC, 1-aminocyclopropane-l-carboxylic acid B, breaker stage... 

Glick BG, CB Jacobson, MML Schwarze, JJ Pasternak (1994) 1-Aminocyclopropane-l-carboxylic acid deaminase mutants of the plant growth promoting rhizobacterium Pseudomonas putida GR12-2 do not stimulate canola root elongation. Can J Microbiol 40 911-915. 

Hot water treatment was reported to delay carotenoid synthesis and thus yellowing of broccoli florets (at 40°C for 60 min) and kale (at 45°C for 30 min), but did not affect Brussels sprouts (Wang 2000). Hot air treatment (38°C and 95% RH for 24 hr) slightly decreased lycopene and (3-carotene content in tomato fruit (Yahia and others 2007) however, fruit heated at 34°C for 24 hr and stored 20°C developed higher lycopene and (3-carotene than nonheated fruit (Soto-Zamora and others 2005). Moist (100% RH) hot air (48.5 or 50°C) for 4 hr caused injury to papaya and losses in lycopene and (3-carotene, but similar treatment with dry air (50% RH), alone or in combination with thiabendazole, had no effect on lycopene and (3-carotene (Perez-Carrillo and Yahia 2004). High-temperature treatment also suppressed 1-aminocyclopropane-l-carboxylic acid oxidase activity and thus indirectly prevented carotenoid synthesis (Suzuki and others 2005). 

The nonprotein amino acid, 1-aminocyclopropane-l-carboxylic acid, is an intermediate of ethylene biosynthesis in plants. This amino acid is synthesized from the L-a-amino acid methionine through the intermediate 5 -adenosyl-L-methionine (SAM) (Scheme 8). ... 

The possibility that many organic compounds could potentially be precursors of ethylene was raised, but direct evidence that in apple fruit tissue ethylene derives only from carbons of methionine was provided by Lieberman and was confirmed for other plant species. The pathway of ethylene biosynthesis has been well characterized during the last three decades. The major breakthrough came from the work of Yang and Hoffman, who established 5-adenosyl-L-methionine (SAM) as the precursor of ethylene in higher plants. The key enzyme in ethylene biosynthesis 1-aminocyclopropane-l-carboxylate synthase (S-adenosyl-L-methionine methylthioadenosine lyase, EC 4.4.1.14 ACS) catalyzes the conversion of SAM to 1-aminocyclopropane-l-carboxylic acid (ACC) and then ACC is converted to ethylene by 1-aminocyclopropane-l-carboxylate oxidase (ACO) (Scheme 1). 

Subsequently, the asymmetric synthesis of stereospecifically monodeu-terated 1-aminocyclopropane-l-carboxylic acids (IS, 2R) and (IS, 2S) has also been achieved by a modification of the above route (89JOC270). The essential step involves an intramolecular alkylation on a lactim ether anion (Scheme 64). 

A few natural products which contain the cyclopropyl ring have been synthesized through metal catalysed cyclopropanation using dicarbonyl diazomethanes. ( )-Cycloeudesmol 63, isolated from marine alga Chondria oppositiclada, was synthesized via a sequence involving a copper catalysed cyclopropanation of a-diazo-/8-ketoester 61 to give the key intermediate 62 (equation 73)1 7,108. Similarly, the bicyclo[3.1.0]hexane derivative 65 was synthesized from the corresponding a-diazo-/8-ketoester 64 via the catalytic method and was converted into ( )-trinoranastreptene 66 (equation 74)109. Intramolecular cyclopropanation of -diazo-/i-ketoesters 67 results in lactones 68 which are precursors to 1-aminocyclopropane-l-carboxylic acids 69 (equation 75)110. 

Adams, D.O. Yang, S.F. (1979). Ethylene biosynthesis identification of 1-aminocyclopropane-l-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc. Natl. Acad. Sci. USA 76, 170-174. 

Burroughs, L.F. (1957). 1-aminocyclopropane-l-carboxylic acid a new amino acid in perry pears and cider apples. Nature (London) 179, 360-361. 

Kondo S, Inoue K. 1997. Abscisic acid (ABA) and 1-aminocyclopropane-l -carboxylic acid (ACC) content during growth of Satohnishiki cherry fruit, and the effect of ABA and ethephon application on fruit quality. J Hortic Sci 72 221-227. 

Methionine is the major precursor in the biochemical pathway to ethylene (9). Ethylene is formed from carbons 3 and 4 of methionine which is degraded in reactions possibly involving free radicals and oxygen (9). Recently Adams and Yang (10,11) identified S-adenosylmethionine (SAM) and 1-aminocyclopropane-l-carboxylic acid (ACC) as intermediates in the pathway from methionine to ethylene. The sequence of reactions in the pathway... 

In contrast to the restricted occurrence of the secondary metabolites mentioned previously, all plants contain 1-amino-cyclopropane-l-carboxylic acid. This amino acid is the precursor of ethylene. In the course of the bios)mthesis of this gaseous phytohormone, 1-aminocyclopropane-l-carboxylic acid is oxidized and decomposed to yield ethylene, HCN, CO2 and water (John, 1997). 

C. Enzymic Fragmentation of 1-Aminocyclopropane-l-carboxylic Acid (ACPC)... 

Most of the compounds cited in this introductory section are produced in metabolic processes where the cyclopropane-containing metabolite appears to be the stable end product or secondary product with as yet unobvious metabolic function. However, this is not the case in at least two types of systems, in which cyclopropyl species are key and necessary intermediate structures in high flux metabolic pathways. The first example is the squalene (76) and phytoene (88) biosynthesis where presqualene pyrophosphate (77) and prephytoene pyrophosphate (89) are obligate cyclopropanoid intermediates in the net head-to-head condensations of two farnesyl pyrophosphate (73) or two geranylgeranyl pyrophosphate (66) molecules respectively. The second example is in plant hormone metabolism where C(3) and C(4) of the amino acid methionine are excised as the simple hormone ethylene via intermediacy of 1-aminocyclopropane-l-carboxylic acid (9). Both examples will be discussed in detail in the Section II. 

Aminocyclopropane- -carboxylic Acid. The acetyl derivative (170 mg) in H2O (2mL) and coned HCl (1 mL) was heated under reflux for 4 h. The mixture was evaporated to dryness under vacuum, the crystalline residue dissolved in H2O, and passed down an anion exchange column (IR-4B, 10 g, 20-50 mesh). Evaporation of the eluate in vacuo gave 1-aminocyclopropane-l-carboxylic acid as colorless crystals yield 87 mg (73%) mp 299-231 °C (HjO/EtOH). 

Transverse geotropism in stems is a characteristic response to ethylene. It has been reported that treatments with epibrassinolide at concentrations of 1-10 ppm accelerated ethylene production in etiolated mung bean hypocotyl segments by increasing ACC (1-aminocyclopropane-l-carboxylic acid) (7). Thus it is possible that the transverse geotropism and even the twining growth response evoked by brassinolide at 10 1-10° ppm were related to the production of ethylene. 

Ethylene is a single, gaseous compound. It is produced when methionine is first converted to S-adenosylmethionine, and then to 1-aminocyclopropane-l-carboxylic acid (ACC) by... 

---