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Biosynthesis of Terpenoids

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Natural Products

Abstract

Terpenes form the largest and structurally one of the most intriguing classes of natural products. When looking at their structures, it becomes clear that the evolution of terpene biosynthesis must have been one of the biggest challenges for Mother Nature, but her solutions are – as often – surprisingly simple. As will be discussed in this chapter, all terpenes are made up from only two five-carbon monomers that have an intrinsic reactivity for the formation of oligomeric linear chains. Virtually the same reactivity is used in cyclization reactions that convert the linear precursors into (poly)cyclic products, not only with introduction of usually several stereogenic centers but also via cationic intermediates in an aqueous environment. How this works – you will find it here.

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Abbreviations

CDP-ME:

4-Diphosphocytidyl-2-C-methyl-d-erythritol

CDP-MEP:

4-Diphosphocytidyl-2-C-methyl-d-erythritol 2-phosphate

CMP:

Cytidine monophosphate

CPP:

Copalyl diphosphate

CTP:

Cytidine triphosphate

DecPP:

Decaprenyl diphosphate

DMAPP:

Dimethylallyl diphosphate

DMASPP:

Dimethylallyl thiodiphosphate

DXP:

1-Deoxy-d-xylulose 5-phosphate

FMN:

Flavin mononucleotide

FPP:

Farnesyl diphosphate

GGPP:

Geranylgeranyl diphosphate

GPP:

Geranyl diphosphate

HexPP:

Hexaprenyl diphosphate

HMBPP:

(E)-4-Hydroxy-3-methylbut-2-enyl diphosphate

HMG-CoA:

3-Hydroxy-3-methylglutaryl-coenzyme A

IDI:

Isopentenyl diphosphate-dimethylallyl diphosphate isomerase

IPP:

Isopentenyl diphosphate

LPP:

Linalyl diphosphate

MEcPP:

2-C-Methyl-d-erythritol 2,4-cyclodiphosphate

MEP:

2-C-Methyl-d-erythritol 4-phosphate

MVA:

(R)-Mevalonic acid

NPP:

Nerolidyl diphosphate

OctPP:

Octaprenyl diphosphate

OSC:

Oxidosqualene cyclase (Lanosterol synthase)

SHC:

Squalene/hopene cyclase

SPP:

Solanyl diphosphate (Nonaprenyl diphosphate)

TIM:

Triosephosphate isomerase

TPP:

Thiamine diphosphate

UPP:

Undecaprenyl diphosphate

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Authors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, Braunschweig, 38106, Germany

    Nelson L. Brock & Prof. Jeroen S. Dickschat

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  1. Nelson L. Brock
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  2. Prof. Jeroen S. Dickschat
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Correspondence to Jeroen S. Dickschat .

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  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Brock, N.L., Dickschat, J.S. (2013). Biosynthesis of Terpenoids. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_121

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