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

Abstract

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.

Authors:
 [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)
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States). Positron Emission Tomography (PET) Facility
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1167431
Alternate Identifier(s):
OSTI ID: 1433587
Report Number(s):
BNL-107233-2014-JA
Journal ID: ISSN 0040-4039; R&D Project: MO-085; KP1602010
Grant/Contract Number:  
DE-SC00112704
Resource Type:
Accepted Manuscript
Journal Name:
Tetrahedron Letters
Additional Journal Information:
Journal Volume: 56; Journal Issue: 3; Journal ID: ISSN 0040-4039
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
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

Citation Formats

Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, and Fowler, Joanna S.. Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid. United States: N. p., 2014. Web. https://doi.org/10.1016/j.tetlet.2014.12.014.
Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, & Fowler, Joanna S.. Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid. United States. https://doi.org/10.1016/j.tetlet.2014.12.014
Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, and Fowler, Joanna S.. Fri . "Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid". United States. https://doi.org/10.1016/j.tetlet.2014.12.014. https://www.osti.gov/servlets/purl/1167431.
@article{osti_1167431,
title = {Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid},
author = {Lee, Sojeong and Qu, Wenchao and Alexoff, David L. and Shea, Colleen and Kim, Dohyun and Schueller, Michael and Fowler, Joanna S.},
abstractNote = {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.},
doi = {10.1016/j.tetlet.2014.12.014},
journal = {Tetrahedron Letters},
number = 3,
volume = 56,
place = {United States},
year = {2014},
month = {12}
}

Journal Article:

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Cited by: 2 works
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Works referenced in this record:

Identity of the Growth-Promoting and Root-Forming Substances of Plants
journal, January 1935

  • Thimann, Kenneth V.; Koepfli, J. B.
  • Nature, Vol. 135, Issue 3403
  • DOI: 10.1038/135101a0

Tryptophan-dependent indole-3-acetic acid biosynthesis by ‘IAA-synthase’ proceeds via indole-3-acetamide
journal, March 2009


Induced carbon reallocation and compensatory growth as root herbivore tolerance mechanisms: Induced root herbivore tolerance
journal, June 2014

  • Robert, Christelle A. M.; Ferrieri, Richard A.; Schirmer, Stefanie
  • Plant, Cell & Environment, Vol. 37, Issue 11
  • DOI: 10.1111/pce.12359

Methyl jasmonate elicits rapid changes in carbon and nitrogen dynamics in tomato
journal, August 2010


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
journal, January 2005

  • Herth, Matthias M.; Thorpe, Michael R.; Ferrieri, Richard A.
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 48, Issue 5
  • DOI: 10.1002/jlcr.933

Optimizing [13N]N2 radiochemistry for nitrogen-fixation in root nodules of legumes
journal, June 2010

  • Kasel, Mirjam C. K.; Schueller, Michael J.; Ferrieri, Richard A.
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 53, Issue 9
  • DOI: 10.1002/jlcr.1786

Radiosynthesis of C-11 labeled auxin (3-indolyl[1-11C]acetic acid) and its derivatives from gramine
journal, June 2011

  • Reid, Alicia E.; Kim, Sung Won; Seiner, Brienne
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 54, Issue 8
  • DOI: 10.1002/jlcr.1894

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

  • Snyder, H. R.; Pilgrim, Frederick J.
  • Journal of the American Chemical Society, Vol. 70, Issue 11
  • DOI: 10.1021/ja01191a067

Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications
journal, September 2009

  • Lee, Ji Woong; Yan, Hailong; Jang, Hyeong Bin
  • Angewandte Chemie International Edition, Vol. 48, Issue 41
  • DOI: 10.1002/anie.200903903

Lithium hydroxide/aqueous methanol: mild reagent for the hydrolysis of bile acid methyl esters
journal, May 1990


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    Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor
    journal, April 2018

    • Xu, Youwen; Cankaya, Aylin Sibel; Hoque, Ruma
    • Chemistry - A European Journal, Vol. 24, Issue 26
    • DOI: 10.1002/chem.201801029

    Acid and 1, 2‐Dichloroethane Co‐Promoted Substitution of the Amino Groups in Gramine and its Analogues with Trialkyl Phosphites
    journal, December 2019