1,2-dehydroreticuline synthase

Class of enzymes 1,2-dehydroreticuline synthase 1.14.19.54 1,2-dehydroreticuline synthase (1.14.19.54) and CYP Symbol CYP82Y2 (cytochrome P450, family 82, member Y2), is an enzyme isolated from the opium poppy Papaver somniferum and the field poppy Papaver rhoeas that catalyzes the chemical reaction:1.14.19.54Hirata K. Poeaknapo C. Schmidt J. Zenk M. H. 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway Phytochemistry 2004 65 8 1039–1046 10.1016/j.phytochem.2004.02.015 15110683 Farrow Scott C. Hagel Jillian M. Beaudoin Guillaume A W. Burns Darcy C. Facchini Peter J. Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy Nature Chemical Biology 2015 11 9 728–732 10.1038/nchembio.1879 26147354 65% Q6122828 (S)-reticuline + NADPH O2 2 H2O Q27103030 reticulinylium cation + NADP+ The three substrates of this enzyme are (S)-reticuline, reduced nicotinamide adenine dinucleotide phosphate (NADPH) and oxygen. Its products are 1,2-dehydroreticulinium cation, oxidised NADP+, and water. The enzyme from field poppy is specific for the (S) enantiomer of reticuline. In the opium poppy, this enzyme forms a fusion protein with 1,2-dehydroreticulinium reductase (NADPH), which immediately converts the reticulinylium cation into {R)-reticuline. The overall result is that (S)-reticuline is converted to {R)-reticuline, which is the precursor of salutaridine, on the pathway to morphine.Winzer Thilo Kern Marcelo King Andrew J. Larson Tony R. Teodor Roxana I. Donninger Samantha L. Li Yi Dowle Adam A. Cartwright Jared Bates Rachel Ashford David Thomas Jerry Walker Carol Bowser Tim A. Graham Ian A. Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein Science 2015 349 6245 309–312 10.1126/science.aab1852 26113639 Hawkins Kristy M. Smolke Christina D. Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae Nature Chemical Biology 2008 4 9 564–573 10.1038/nchembio.105 18690217 2830865 This gene fusion event has been suggested to evolve only once, about 20 million years ago.Tian Ya Kong Lingzhe Li Qi Wang Yifan Wang Yongmiao An Zhoujie Ma Yuwei Tian Lixia Duan Baozhong Sun Wei Gao Ranran Chen Shilin Xu Zhichao Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids Natural Product Reports 2024 41 11 1787–1810 10.1039/d4np00029c 39360417 Carr Samuel C. Rehman Fasih Hagel Jillian M. Chen Xue Ng Kenneth K. S. Facchini Peter J. Two ubiquitous aldo-keto reductases in the genus Papaver support a patchwork model for morphine pathway evolution Communications Biology 2024 7 1 1410 10.1038/s42003-024-07100-w free 39472466 11522673 70% Q6122828 (S)-reticuline Q82096614 (R)-reticuline salutaridine 0.5 The enzyme is a hemoprotein of cytochrome P450 type. References Category:EC 1.14.19 Category:Cytochrome P450 Family 8