Hexaprenyl diphosphate synthase from Micrococcus luteus B-P 26 (Ml-HexPPs) is a heterooligomeric type trans-prenyltransferase catalyzing consecutive head-to-tail condensations of three molecules of isopentenyl diphosphates (C(5)) on a farnesyl diphosphate (FPP; C(15)) to form an (all-E) hexaprenyl diphosphate (HexPP; C(30)). Ml-HexPPs is known to function as a heterodimer of two different subunits, small and large subunits called HexA and HexB, respectively. Compared with homooligomeric trans-prenyltransferases, the molecular mechanism of heterooligomeric trans-prenyltransferases is not yet clearly understood, particularly with respect to the role of the small subunits lacking the catalytic motifs conserved in most known trans-prenyltransferases. We have determined the crystal structure of Ml-HexPPs both in the substrate-free form and in complex with 7,11-dimethyl-2,6,10-dodecatrien-1-yl diphosphate ammonium salt (3-DesMe-FPP), an analog of FPP. The structure of HexB is composed of mostly antiparallel α-helices joined by connecting loops. Two aspartate-rich motifs (designated the first and second aspartate-rich motifs) and the other characteristic motifs in HexB are located around the diphosphate part of 3-DesMe-FPP. Despite the very low amino acid sequence identity and the distinct polypeptide chain lengths between HexA and HexB, the structure of HexA is quite similar to that of HexB. The aliphatic tail of 3-DesMe-FPP is accommodated in a large hydrophobic cleft starting from HexB and penetrating to the inside of HexA. These structural features suggest that HexB catalyzes the condensation reactions and that HexA is directly involved in the product chain length control in cooperation with HexB.
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http://dx.doi.org/10.1074/jbc.M110.147991 | DOI Listing |
Int J Mol Sci
August 2022
Department of Bioinformatics, Matthias Schleiden Institute, University of Jena, Ernst-Abbe-Platz 2, 07743 Jena, Germany.
A coiled coil is a structural motif in proteins that consists of at least two α-helices wound around each other. For structural stabilization, these α-helices form interhelical contacts via their amino acid side chains. However, there are restrictions as to the distances along the amino acid sequence at which those contacts occur.
View Article and Find Full Text PDFTrends Biochem Sci
November 2022
Université d'Angers, Université de Bretagne Occidentale, Institut de Recherche Fondamentale (IRF), Structure Féderative de Recherche (SFR) Interactions Cellulaires et Applications Thérapeutiques (ICAT), 49000 Angers, France. Electronic address:
Triterpenes are C30 organic compounds abundantly found in all living organisms. Although previously believed to be exclusively produced from squalene or oxidosqualene, a recent report by Tao and colleagues describes a new triterpene biosynthetic route involving the cyclization of the precursor hexaprenyl diphosphate (HexPP) by unprecedented bifunctional terpene synthase (TS) enzymes.
View Article and Find Full Text PDFNature
June 2022
Department of Urology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan, China.
All known triterpenes are generated by triterpene synthases (TrTSs) from squalene or oxidosqualene. This approach is fundamentally different from the biosynthesis of short-chain (C-C) terpenes that are formed from polyisoprenyl diphosphates. In this study, two fungal chimeric class I TrTSs, Talaromyces verruculosus talaropentaene synthase (TvTS) and Macrophomina phaseolina macrophomene synthase (MpMS), were characterized.
View Article and Find Full Text PDFACS Synth Biol
March 2019
Department of Applied Chemistry and Biotechnology , Chiba University, 263-8522 Chiba , Japan.
Longer-chain carotenoids have interesting physiological and electronic/photonic properties due to their extensive polyene structures. Establishing nonnatural biosynthetic pathways for longer-chain carotenoids in engineerable microorganisms will provide a platform to diversify and explore the potential of these molecules. We have previously reported the biosynthesis of nonnatural C carotenoids by engineering a C-carotenoid backbone synthase (CrtM) from Staphylococcus aureus.
View Article and Find Full Text PDFMar Drugs
September 2017
Department of Medicinal Chemistry, University of Utah, 30 S. 2000 E., Salt Lake City, UT 84112, USA.
Hydroquinone meroterpenoids, especially those derived from marine sponges, display a wide range of biological activities. However, use of these compounds is limited by their inaccessibility; there is no sustainable supply of these compounds. Furthermore, our knowledge of their metabolic origin remains completely unstudied.
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