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Structural and Mechanistic Insight into Terpene Synthases that Catalyze the Irregular Non‐Head‐to‐Tail Coupling of Prenyl Substrates
Author(s) -
Kobayashi Masaya,
Kuzuyama Tomohisa
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800510
Subject(s) - prenylation , terpenoid , terpene , stereochemistry , hydroxylation , geranylgeraniol , chemistry , farnesyl diphosphate synthase , prenyltransferase , farnesol , biosynthesis , biochemistry , enzyme
Terpenoids have diverse structures and thus represent an important class of biologically active natural products. The structural diversity of terpenoids originates from the coupling of prenyl diphosphate substrates, such as isopentenyl diphosphate and dimethylallyl diphosphate. These isoprenyl diphosphates undergo canonical and sequential “head‐to‐tail” coupling catalyzed by terpene synthases, followed by modifications such as cyclization, hydroxylation, and glycosylation. In recent years, several terpene synthases that catalyze irregular “non‐head‐to‐tail” couplings to afford branched terpenoids have been identified. This minireview describes structural and mechanistic insights into these unusual coupling reactions that provide a new strategy for the structural diversification of natural products.