Strictosidine synthase

Fig. 10.1 Reaction catalyzed by strictosidine synthase (Str) in monoterpenoid indole alkaloid formation.

KUTCHAN, T.M., HAMPP, N., LOTTSPEICH, F., BEYREUTHER, K., ZENK, M.H., The cDNA clone for strictosidine synthase from Rauvolfia serpentina - DNA sequence determination and expression in Escherichia col., FEBSLett., 1988, 237,40-44. 

PFITZNER, U., ZENK, M.H., Immobilization of strictosidine synthase from Catharanthus cell cultures and preparative synthesis of strictosidine, Planta Med., 1982, 46,10-14. 

HAMPP, N., ZENK, M.H., Homogeneous strictosidine synthase from cell suspension cultures of Rauvolfia serpentina, Phytochemistry, 1988,27, 3811-3815. 

KUTCHAN, T.M., Expression of enzymatically active cloned strictosidine synthase from the higher plant Rauvolfia serpentina in Escherichia coli, FEBS Lett., 1989, 257, 127-130. 

KUTCHAN, T.M., BOCK, A., DITTRICH, H., Heterologous expression of strictosidine synthase and berberine bridge enzyme in insect cell culture, Phytochemistry, 1994, 35, 353-360. 

Scheme 22. The enzymatic synthesis of strictosidine (86) by immobilized strictosidine synthase.

The enzyme responsible for the stereospecific condensation of trypt-amine and secologanin 34) was called strictosidine synthase, and its presence was demonstrated by Treimer and Zenk 194) in a number of indole alkaloid-producing plants, including Amsonia salicifolia, Catharanthus roseus, Ochrosia elliptica, Rauwolfia vomitoria, Rhazya orientalis, Stem-madenia tomentosa. Vinca minor, and Voacanga africana. Enzyme activity as high as 1698 pkat/mg protein was observed for O. elliptica. No... 

Strictosidine synthase Catharanthus roseus Rauvoljia serpentina... 

Bracher, D. and Kutchan, T. M. 1992. Strictosidine synthase from Rauvolfia serpentina Analysis of a gene involved in indole alkaloid biosynthesis. Archives of Biochemistry and Biophysics, 294 717-723. 

Fig. 6 In vivo reprogramming of alkaloid biosynthesis in hairy roots of C. roseus by introduction of a mutant cDNA of the key enzyme strictosidine synthase (STR) with broader, unnatural substrate specificity leading to diversification of alkaloid content in roots following long-term feeding with 5-substituted tryptamines (X = Cl, Br, Me) [78]...

The power of engineered enzymes in the synthesis of novel alkaloids, to generate structural diversity and establish new alkaloid libraries, is best represented by the enzyme strictosidine synthase (STR1). 

Fig. 3. Biosynthesis of TIAs in C. roseus. Solid arrows indicate single enzymatic conversions, whereas dashed arrows indicate multiple enzymatic conversions. AS Anthranilate synthase, DXS D-l-deoxyxylulose 5-phosphate synthase G10H geraniol 10-hydroxylase CPR cytochrome P450 reductase TDC tryptophan decarboxylase STR strictosidine synthase SGD strictosidine /1-D-glucosidase D4H desacetoxyvindoline 4-hydroxylase DAT acetyl-CoA 4-O-deacetylvindoline 4-O-acetyl transferase. Genes regulated by ORCA3 are underlined. Reprinted with permission from [91]. Copyright (2000) American Association for the Advancement of Science...

Figure 7.7 The relative location of c/s-elements and putative transcriptional regulators on the tryptophan decarboxylase (TDC), strictosidine synthase (STR), and cytochrome P450 reductase (CPR) gene promotors from Catharanthus roseus. The black box represents elements responsive to elicitor, jasmonate, or UV light. The white box represents a G-box motif, whereas the striped box represents a GCC-box element.

MCKNIGHT, T.D., ROESSNER, C.A., DEVAGUPTA, R SCOTT, A.I., NESSLER, C.L., Nucleotide sequence of a cDNA encoding the vacuolar protein strictosidine synthase from Catharanthus roseus. Nucleic Acids Res., 1990, 18, 4939. 

EILERT, U., DE LUCA, V., CONSTABEL, F., KURZ, W.G.W., Elicitor-mediated induction of tryptophan decarboxylase and strictosidine synthase activities in cell suspension cultures of Catharanthus roseus. Arch Biochem. Biophys., 1987, 254,491-497. 

PASQUALI, G ERVEN, A.S., OUWERKERK, P.B., MENKE, F.L., MEMELINK, J., The promoter of the strictosidine synthase gene from periwinkle confers elicitor-inducible expression in transgenic tobacco and binds nuclear factors GT-1 and GBF. Plant Mol. Biol., 1999,39, 1299-1310. 

OUWERKERK, P.B., MEMELINK, J., A G-box element from the Catharanthus rosues strictosidine synthase (Str) gene promoter confers seed-specific expression in transgenic tobacco plants. Mol. Gen. Genet., 1999,261, 635-643. 

SIBERIL, Y BENHAMRON, S., MEMELINK, J., GIGLIOLI-GUIVARC H, N., THIERSAULT, M., BOISSON, B., DOIREAU, P GANTET, P, Catharanthus roseus G-box binding factors 1 and 2 act as repressors of strictosidine synthase gene expression in cell cultures. Plant Mol. Biol., 2001, 45, 477-488. 

CANEL, C., LOPES-CARDOSO, M.I., WH1TMER, S VAN DER FITS, L., PASQUALI, G., VAN DER HEIJDEN, R HOGE, J.H., VERPOORTE, R., Effects of over-expression of strictosidine synthase and tryptophan decarboxylase on alkaloid production by cell cultures of Catharanthus roseus. Planta, 1998,205, 414-419. 

STEVENS, L.H., BLOM, T.J.M., VERPOORTE, R., Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and Tabemaemontana divaricata. Plant Cell Rep., 1993,12, 563-576. 

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