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Title: Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid

Journal Article · · Tetrahedron Letters
 [1];  [2];  [2];  [2];  [2];  [2];  [2]
  1. Brookhaven National Laboratory (BNL), Upton, NY (United States); Stony Brook Univ., Stony Brook, NY (United States)
  2. Brookhaven National Laboratory (BNL), Upton, NY (United States)
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An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([11]IAA or [11]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11]cyanation and alkaline hydrolysis reactions were performed consecutively in a single pot without a time-consuming intermediate purification step. The entire production time for this updated procedure is 55 min, which dramatically simplifies the entire synthesis and reduces the starting radioactivity required for a whole plant imaging study.

Research Organization:
Brookhaven National Lab. (BNL), Upton, NY (United States). Positron Emission Tomography (PET) Facility
Sponsoring Organization:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
Grant/Contract Number:
DE-SC00112704
OSTI ID:
1167431
Alternate ID(s):
OSTI ID: 1433587
Report Number(s):
BNL-107233-2014-JA; R&D Project: MO-085; KP1602010
Journal Information:
Tetrahedron Letters, Vol. 56, Issue 3; ISSN 0040-4039
Publisher:
ElsevierCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 7 works
Citation information provided by
Web of Science

References (14)

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11C-imaging: methyl jasmonate moves in both phloem and xylem, promotes transport of jasmonate, and of photoassimilate even after proton transport is decoupled journal March 2007
Use of carbon-11 in Populus shows that exogenous jasmonic acid increases biosynthesis of isoprene from recently fixed carbon journal May 2005
Synthesis of the phytohormone [11C]methyl jasmonate via methylation on a C18 Sep Pak? cartridge
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  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 48, Issue 5 https://doi.org/10.1002/jlcr.933
journal January 2005
Optimizing [13N]N2 radiochemistry for nitrogen-fixation in root nodules of legumes
  • Kasel, Mirjam C. K.; Schueller, Michael J.; Ferrieri, Richard A.
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 53, Issue 9 https://doi.org/10.1002/jlcr.1786
journal June 2010
Radiosynthesis of C-11 labeled auxin (3-indolyl[1-11C]acetic acid) and its derivatives from gramine journal June 2011
Radiosynthesis of 3-indolyl[1-11C]acetic acid for phyto-PET-imaging: An improved production procedure and formulation method journal September 2014
The Preparation of 3-Indoleacetic Acid; A New Synthesis of Tryptophol journal November 1948
Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications journal September 2009
Lithium hydroxide/aqueous methanol: mild reagent for the hydrolysis of bile acid methyl esters journal May 1990

Cited By (2)

Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor journal April 2018
Acid and 1, 2‐Dichloroethane Co‐Promoted Substitution of the Amino Groups in Gramine and its Analogues with Trialkyl Phosphites journal December 2019

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Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
Carbon-11 labeled indole-3-acetic acid
nucleophilic [11C]cyanation
tetraethylene glycol
two-step one-pot
positron emission tomography (PET) facility