Entry Name (S)-8-oxocitronellyl enol synthase;
Class Oxidoreductases;BRITE hierarchy
Sysname (S)-8-oxocitronellyl enol:NAD(P)+ oxidoreductase
Reaction(IUBMB) (S)-8-oxocitronellyl enol + NAD(P)+ = (6E)-8-oxogeranial + NAD(P)H + H+ [RN:
R12517 R12518 ]
Reaction(KEGG) Substrate Product Comment Isolated from the plants Catharanthus roseus, Olea europaea (common olive), and several Nepeta species. The enzyme reduces 8-oxogeranial, generating an unstable product that is subsequently cyclized into several possible products, either non-enzymically or by dedicated cyclases. The products, known as iridoids, are involved in the biosynthesis of many indole alkaloids. cf. EC
1.3.1.123 , 7-epi-iridoid synthase.
History EC 1.3.1.122 created 2013 as EC 1.3.1.99, part transferred 2019 to EC 1.3.1.122
Pathway ec01110 Biosynthesis of secondary metabolites
Orthology K20144 (S)-8-oxocitronellyl enol synthase
Genes Taxonomy Reference Authors Geu-Flores F, Sherden NH, Courdavault V, Burlat V, Glenn WS, Wu C, Nims E, Cui Y, O'Connor SE
Title An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.
Journal Sequence Reference Authors Hu Y, Liu W, Malwal SR, Zheng Y, Feng X, Ko TP, Chen CC, Xu Z, Liu M, Han X, Gao J, Oldfield E, Guo RT
Title Structures of Iridoid Synthase from Cantharanthus roseus with Bound NAD(+) , NADPH, or NAD(+) /10-Oxogeranial: Reaction Mechanisms.
Journal Sequence Reference Authors Alagna F, Geu-Flores F, Kries H, Panara F, Baldoni L, O'Connor SE, Osbourn A
Title Identification and Characterization of the Iridoid Synthase Involved in Oleuropein Biosynthesis in Olive (Olea europaea) Fruits.
Journal Sequence Reference Authors Qin L, Zhu Y, Ding Z, Zhang X, Ye S, Zhang R
Title Structure of iridoid synthase in complex with NADP(+)/8-oxogeranial reveals the structural basis of its substrate specificity.
Journal Sequence Reference Authors Sherden NH, Lichman B, Caputi L, Zhao D, Kamileen MO, Buell CR, O'Connor SE
Title Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry.
Journal Reference Authors Lichman BR, Kamileen MO, Titchiner GR, Saalbach G, Stevenson CEM, Lawson DM, O'Connor SE
Title Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis.
Journal Reference Authors Lichman BR, O'Connor SE, Kries H
Title Biocatalytic Strategies towards [4+2] Cycloadditions.
Journal Other DBs ExPASy - ENZYME nomenclature database: 1.3.1.122
