N-methylputrescine oxidase

McLauchan, W. R., McKee, R. A. and Evans, D. M. 1993. The purification and immunocharacterisation of N-methylputrescine oxidase from transformed root cultures of Nicotiana tabacum L. cv.SC58. Planta, 191 440 45. 

Figure 2.3 Biosynthesis of the tropane alkaloids. PMT, putrescine N-methyltransferase DAO, diamine oxidase MPO, N-methylputrescine oxidase TR I and II, tropinone reductase H6H, hyoascyamine 6-hydroxylase.

Katoh, A., Shoji, T. and Hashimoto, T. (2007) Molecular cloning of N-methylputrescine oxidase from tobacco. Plant Cell Physiol, 48,550. ... 

Teuber M, Azemi ME, Namjoyan F, Meier A-C, Wodak A, Brandt W, Drager B. Putrescine N-methyltransferases—a structure-function analysis. Plant Mol. Biol. 2007 63 787-801. McLauchlan WR, McKee RA, Evans DM. The purification and immunocharacterization of N-methylputrescine oxidase from transformed root cultures of Nicotinia tabacum. Planta 1993 191 440-445. 

McLauchan WR, McKee RA, Evans DM. TTie purificatitHi and immunocharacterisa-tion of N-methylputrescine oxidase from transformed root cultures of Nicotianataba-cum L. CV.SC58. Planta 1993 191 440-5. 

An enzyme that catalyzes the fonnation of 4-N-methyl-aminobutanal from A -methylputrescine has been isolated from several sources. The enzyme that forms the A -methyl-A -pyrrolinium salt (3), N-methylputrescine oxidase, has been isolated from tobacco roots (Leete, 1980, 1990). 

Mizusaki, S., Tanabe, Y., Noguchi, H. et al. (1972) N-methylputrescine oxidase from tobacco roots. Phytochemistry, 11, 2757-2762. 

Naconsie M, Kato K, Shoji T, Hashimoto T (2014) Molecular evolution of N-methylputrescine oxidase in tobacco. Plant Cell Physiol 55 436-444. 

A-methylputrescine oxidase catalyzes the formation of N-methylpyrrolinium cation, an important intermediate of tropane alkaloids biosynthetic pathway as well as of nicotine. Fig. (1). The... 

The first committed biosynthetic step toward pyrrolidine and tropane alkaloids involves N-methylation of putrescine to furnish A-methylputrescine (21) by SAM-dependent putrescine A-methyltransferase (EC 2.1.1.53) (Scheme 11.4) [9, 19, 20]. Oxidative deamination by A-methylputrescine oxidase (EC 1.4.3.21) affords 4-methylaminobutanal (22), which spontaneously cyclizes to furnish the corresponding A-methyl-A -pyrrolinium cation (23) via intramolecular Schiff-base formation. Although no enzymes have been identified catalyzing the subsequent biosynthetic steps, from... 

Heim WG, Sykes KA, Hildreth SB et al (2007) Cloning and characterization of a Nicotiana taba-cum methylputrescine oxidase transcript. Phytochemistry 68 454-463 Hibi N, Higashiguchi S, Hashimoto T et al (1994) Gene expression in tobacco low-nicotine mutants. Plant Cell 6 723-735... 

Scheme 13.17. A cartoon showing the possible formation of the N-methyl-A -pyrrohum cation from a topaquinone-bound oxidant and the AT-methylputrescine cation. This process is catalyzed by a primary amine oxidase (EC 1.4.3.21). Additional information can be found at Dooley, D. M. /. Biol. Inorg. Chem., 2008, 4,1 and Heim, W. G. Sykes, K. A. Hildreth, S. B. Sun, 1 Lu, R.-H. Jelsko, J. G. Phytochemistry, 2007,68,454.

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