Aminocyclopropane-1-carboxylic acid

Scheme 1 The ethylene biosynthetic pathway. The enzymes catalyzing each step are shown above the arrows. SAM S-adenosyl-L-methionine SAMS S-adenosyl-i-methionine synthetase ACC 1-aminocyclopropane-1-carboxylic acid ACS 1-aminocyclopropane-1-carboxylate synthase ACO 1-aminocyclopropane-1-carboxylate oxidase Ade adenine MTA methylthioadenosine. The atoms of SAM recycled to methionine through methionine cycle are marked in red and the atoms of methionine converted to ethylene are marked in bold. For details see text.

NT564 Grady, K. L., and J. A. Bassham. 1-Aminocyclopropane-1 -carboxylic acid concentrations in shoot-forming and non-shoot forming tobacco callus NT575 cultures. Plant Physiol 1982 70 ... 

A similar 3-(2-bromoethyl) derivative has been utilized to synthesize 1-aminocyclopropane-1 -carboxylic acid by an intramolecular base-catalyzed cyclization. This was possible when position 6 was blocked by the presence of two substituents. Some unexpected stereochemical results also came up in this study (85MI2). The starting material was the piperazine-2,5-dione derived from (/ )-(+ )-2-methyl-3-phenylalanine and glycine. The bislactim ether derived from this, on treatment with butyl lithium in THF at -78°C, gave the lithio derivative. Alkylation of this with 2-haloethyl... 

Aminocyclopropane-1-carboxylic acid 4.59 a-Aminobutyric acid 10.99 3,5-Dibromotyrosine 18.43... 

Figure 3. Model of the mode of action of auxin herbicides in the induction of growth inhibition, tissue damage and senescence in dicot plant species, as illustrated for cleavers Galium aparine). ABA, abscisic acid ACC, 1 -aminocyclopropane-1 -carboxylic acid ROS, reactive oxygen species SAM, S-adenosylmethionine. Modified fiom [20,41],...

In this section we analyze information about metabolic cleavage or breakdown of cyclopropane rings in three instances the biosynthesis of irregular monoterpenes, the ringopening of cycloartenol (20) derivatives, and the metabolic opening of 1-aminocyclopropane-1-carboxylic acid (ACPC) (9) by two quite distinct fragmentation routes. We will not explicitly discuss the processing of presqualene pyrophosphate (77) and prephytoene pyrophosphate (89) to squalene (76) and phytoene (88) respectively, since those transformations have already been dealt with in Section II. 

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

IR-Coronamic acid (505) and U -allocoronamic acid (649) were more effectively converted to the 1-malonyl derivative than the two IS-stereoisomers From this stereoselectivity it was deduced that aminocyclopropanecarboxylic acid (6) is recognized as a D-amino acid by malonyl transferase. For resolution of racemic 2-alkyl-1-aminocyclopropane-1-carboxylic acids see Refs 27, 33, 752. 

Aminocyclopropane-1-carboxylic acids. These cyclopropyl amino acids can be obtained in high chemical and optical yield by reaction of this ylide with the a, /3-dehydro lactones (3) prepared from (5S,6R)-4-/-butoxycarbonyl-5,6-diphenyl-2,3,5,6-tctrahydro-4W-l,4-oxazin-2-one (2, 14,58-59). The reaction of 3 with the ylide derived from... 

Bouzayen, M., Latche, A., Pech, J.-C., Boiler, T., 1991. Iron an essential cofactor for the conversion of 1-aminocyclopropane-1-carboxylic acid to ethylene. Planta 184, 244-247. 

Liu, X., Li, D. R, Wang, Y, and Lu, Y. T., Determination of 1 -aminocyclopropane-1 -carboxylic acid in apple extracts by capillary electrophoresis with laser-induced fluorescence detection, J. Chromatogr. A, 1061,99, 2004. 

Yang, S. F., The formation of ethylene from 1-aminocyclopropane-1-carboxylic acid, in Ethylene. Biochemical, Physiological and Applied Aspects (Y. Fuchs and E. Chalutz, eds.), 1-10, Nijhoff Junk, The Hague, 1984. 

Peiser, G. D., T. Wang, N. E. Hoffman, S. F. Yang, H. Liu, and C, T. Walsh, Formation of cyanide from carbon 1 of 1-aminocyclopropane-1-carboxylic acid during its conversion to ethylene, Proc. Natl. Acad. Sci. USA, 81, 3059-3063 (1984). 

Two short reports concerning another mononuclear iron (ferrous) centre, 1-aminocyclopropane- 1-carboxylic acid oxidase, abbreviated ACCO, have been presented. This enzyme catalyses the last step in the synthesis of ethylene, a gaseous hormone involved in ripening of plants. One paper deals with spectroscopic techniques including near infrared (NIR) and circular or magnetic circular dichroism applied to the ferrous active site. The other is on preliminary ENDOR data probing the ligation and structure of this site in the ferric state. ... 

Zhang HP, Kayeka H, Osada H. Biosynthesis of 1-aminocyclopropane-1-carboxylic acid moiety on cytotrienin A in Streptomyces sp. Tetrahedron Lett. 1998 39 6947-6948. 

---