Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

Jarchow-Choy, Sarah; Koppisch, Andrew; Fox, David

doi:10.2174/1385272819666140501001101

Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

Journal Article · Tue Jul 01 04:00:00 EDT 2014 · Current Organic Chemistry

DOI:https://doi.org/10.2174/1385272819666140501001101· OSTI ID:1628002

Jarchow-Choy, Sarah ^[1]; Koppisch, Andrew ^[2]; Fox, David ^[3]

Los Alamos National Lab. (LANL), Los Alamos, NM (United States); DOE/OSTI
Northern Arizona Univ., Flagstaff, AZ (United States)
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Isoprenoids constitute the largest class of natural products with greater than 55,000 identified members. They play essential roles in maintaining proper cellular function leading to maintenance of human health, plant defense mechanisms against predators, and are often exploited for their beneficial properties in the pharmaceutical and nutraceutical industries. Most impressively, all known isoprenoids are derived from one of two C5-precursors, isopentenyl diphosphate (IPP) or dimethylallyl diphosphate (DMAPP). In order to study the enzyme transformations leading to the extensive structural diversity found within this class of compounds there must be access to the substrates. Sometimes, intermediates within a biological pathway can be isolated and used directly to study enzyme/pathway function. However, the primary route to most of the isoprenoid intermediates is through chemical catalysis. As such, this review provides the first exhaustive examination of synthetic routes to isoprenoid and isoprenoid precursors with particular emphasis on the syntheses of intermediates found as part of the 2C-methylerythritol 4-phosphate (MEP) pathway. In addition, representative syntheses are presented for the monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), triterpenes (C30) and tetraterpenes (C40). Finally, in some instances, the synthetic routes to substrate analogs found both within the MEP pathway and downstream isoprenoids are examined.

View Accepted Manuscript (DOE)

Research Organization:: Donald Danforth Plant Science Center, St. Louis, MO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: EE0003046

OSTI ID:: 1628002

Journal Information:: Current Organic Chemistry, Journal Name: Current Organic Chemistry Journal Issue: 8 Vol. 18; ISSN 1385-2728

Publisher:: Bentham Science PublishersCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Chemistry
Enzyme mechanism
MEP pathway
isoprenoids
terpenes

Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

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