1- aminocyclopropane-l-carboxylate

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

Belimov AA et al. (2001) Characterization of plant growth promoting rhizobacteria isolated from polluted soils and containing 1-aminocyclopropane-l-carboxylate deaminase. Can J Microbiol Al 642-652. 

Karthikeyan S, Q Zhou, Z Zhao, C-L Kao, Z Tao, H Robinson, H-w Liu, H Zhang (2004) Structural analysis of Pseudomonas 1-aminocyclopropane-l-carboxylate deaminase complexes insight into the mechanism of a unique pyridoxal-5 -phosphate dependent cyclopropane ring-opening reaction. Biochemistry 43 13328-13339. 

Walsh C, RA Pascal, M Johnston, R Raines, D Dikshit, A Krantz, M Houma (1981) Mechanistic studies on the pyridoxal phosphate enzyme 1-aminocyclopropane-l-carboxylate deaminase from Pseudomonas sp. Biochemistry 20 7509-7519. 

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). 

Aminocyclopropane-l-Carboxylate Synthase, an Enzyme of Ethylene Biosynthesis... 

A similar lactone ring opening is involved in the asymmetric synthesis of stereospecifically monodeuterated 1-aminocyclopropane-l-carboxylic... 

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). 

Write out a plausible step-by-step mechanism by which 1-aminocyclopropane-l-carboxylate synthase (ACC synthase) of plant tissues can form ACC from S-adenosylmethionine. This reaction requires a specific cofactor... 

A variety of three-membered carbocycles including cyclopropylcarbonyl and -sulfonyl derivatives, cyclopropylcarbonitriles and -methanols, nitrocyclopropanes, cyclo-propanols and cyclopropylamines have been prepared via the 1,3-elimination of HX. Some representative cyclopropyl derivatives recently prepared by this method are shown in Scheme 116-18 and in equations 8-26. Conversion of chelated homoserine, 5,to chelated 2-amino-4-bromobutyrate and treatment with aqueous base directly affords chelated 1-aminocyclopropane-l-carboxylate (equation 8)19. The 1,3-elimination in 6 interestingly leads to the preferential formation of the cis isomer, from which 7, a key structural element of synthetic pyrethroid insecticides, is obtained (equation 9)20. A sulfur substituent can serve both as an activating group and as a leaving group in this type of reaction and, thus, 1,3-bis(phenylthio)propane affords cyclopropyl phenyl sulfide upon treatment with butyl-... 

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. 

Nakajima, N., Mori, H., Yamazaki, K. Imaseki, H. (1990). Molecular cloning and sequence of a complementary DNA encoding 1-aminocyclopropane-l-carboxylic synthase induced by tissue wounding. Plant Cell Physiology 31, 1021-9. 

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... 

Ethylene is produced not only by higher plants but also by microorganisms. Microorganisms produce ethylene by two different pathways 2-oxoglutarate-dependent pathway926 and 2-oxo-4-methylthiobutyrate-dependent pathway 927 On the other hand, higher plants produce ethylene by ACC (1-aminocyclopropane-l-carboxylic... 

Ko, S., Eliot, A., Kirsch, J. (2004). S-methylmethionine is both a substrate and an activator of 1-aminocyclopropane-l-carboxylate synthase. Arc/t. Biochem. Biophys., 421, 85-90. 

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). 

John, P. (1997) Ethylene biosynthesis the role of 1-aminocyclopropane-l-carboxylate (ACC) oxidase and its possible evolutionary origin. Physiol. Plantarum, 100, 583-92. 

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