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Title: Synthetic Routes to Methylerythritol Phosphate Pathway Intermediates and Downstream Isoprenoids

Journal Article · · Current Organic Chemistry
 [1];  [2];  [1]
  1. Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
  2. Northern Arizona Univ., Flagstaff, AZ (United States)
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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.

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, Vol. 18, Issue 8; ISSN 1385-2728
Publisher:
Bentham Science PublishersCopyright Statement
Country of Publication:
United States
Language:
English

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Cited By (2)

Review of the algal biology program within the National Alliance for Advanced Biofuels and Bioproducts journal March 2017
Genetic resources for advanced biofuel production described with the Gene Ontology journal October 2014

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Related Subjects

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