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Title: Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor

Abstract

The development of a convenient and rapid method to synthesize radiolabeled enantiomerically pure amino acids (AAs) as potential positron emission tomography (PET) imaging agents for mapping various biochemical transformations in living organisms remains as a challenge. This is especially true for the synthesis of carbon-11 labeled AAs given the short half-life of carbon-11 ( 11C, t 1/2 = 20.4 min). A facile synthetic pathway to prepare enantiomerically pure 11C-labeled L-asparagine was developed using a partially protected serine as a starting material with a four-step transformation providing a chiral fivemembered cyclic sulfamidate as the radiolabeling precursor. Its structure and absolute configuration were confirmed by X-Ray crystallography. Utilizing a [ 11C]cyanide nucleophilic ring opening reaction followed by selective acidic hydrolysis and deprotection, enantiomerically pure L-[4- 11C]asparagine was synthesized. Further optimization of reaction parameters, including base, metal ion source, solvent, acid component, reaction temperature and reaction time, a reliable two-step method for synthesizing L-[4- 11C]asparagine was presented; within a 45 ± 3 min (n = 5, from end-of-bombardment), the desired enantiomerically pure product was synthesized with the initial nucleophilic cyanation yield of 69 ± 4% (n = 5) and overall two-step radiochemical yield of 53 ± 2% (n = 5) based on startingmore » [ 11C]HCN, and with radiochemical purity of 96 ± 2% (n = 5).« less

Authors:
 [1];  [2];  [3];  [3];  [1];  [2];  [1];  [3];  [4];  [1];  [2];  [2];  [1]; ORCiD logo [1]
  1. Brookhaven National Lab. (BNL), Upton, NY (United States)
  2. Brookhaven National Lab. (BNL), Upton, NY (United States); Johannes Gutenberg Univ., Mainz (Germany)
  3. Brookhaven National Lab. (BNL), Upton, NY (United States); Stony Brook Univ., NY (United States)
  4. City Univ. (CUNY), NY (United States). Buruch College
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1473635
Report Number(s):
BNL-209073-2018-JAAM
Journal ID: ISSN 0947-6539
Grant/Contract Number:  
SC0012704
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 24; Journal Issue: 26; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Xu, Youwen, Cankaya, Aylin Sibel, Hoque, Ruma, Lee, So Jeong, Shea, Colleen, Kersting, Lena, Schueller, Michael, Fowler, Joanna S., Szalda, David, Alexoff, David, Riehl, Barbara, Gleede, Tassilo, Ferrieri, Richard A., and Qu, Wenchao. Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor. United States: N. p., 2018. Web. doi:10.1002/chem.201801029.
Xu, Youwen, Cankaya, Aylin Sibel, Hoque, Ruma, Lee, So Jeong, Shea, Colleen, Kersting, Lena, Schueller, Michael, Fowler, Joanna S., Szalda, David, Alexoff, David, Riehl, Barbara, Gleede, Tassilo, Ferrieri, Richard A., & Qu, Wenchao. Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor. United States. doi:10.1002/chem.201801029.
Xu, Youwen, Cankaya, Aylin Sibel, Hoque, Ruma, Lee, So Jeong, Shea, Colleen, Kersting, Lena, Schueller, Michael, Fowler, Joanna S., Szalda, David, Alexoff, David, Riehl, Barbara, Gleede, Tassilo, Ferrieri, Richard A., and Qu, Wenchao. Mon . "Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor". United States. doi:10.1002/chem.201801029. https://www.osti.gov/servlets/purl/1473635.
@article{osti_1473635,
title = {Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor},
author = {Xu, Youwen and Cankaya, Aylin Sibel and Hoque, Ruma and Lee, So Jeong and Shea, Colleen and Kersting, Lena and Schueller, Michael and Fowler, Joanna S. and Szalda, David and Alexoff, David and Riehl, Barbara and Gleede, Tassilo and Ferrieri, Richard A. and Qu, Wenchao},
abstractNote = {The development of a convenient and rapid method to synthesize radiolabeled enantiomerically pure amino acids (AAs) as potential positron emission tomography (PET) imaging agents for mapping various biochemical transformations in living organisms remains as a challenge. This is especially true for the synthesis of carbon-11 labeled AAs given the short half-life of carbon-11 (11C, t1/2 = 20.4 min). A facile synthetic pathway to prepare enantiomerically pure 11C-labeled L-asparagine was developed using a partially protected serine as a starting material with a four-step transformation providing a chiral fivemembered cyclic sulfamidate as the radiolabeling precursor. Its structure and absolute configuration were confirmed by X-Ray crystallography. Utilizing a [11C]cyanide nucleophilic ring opening reaction followed by selective acidic hydrolysis and deprotection, enantiomerically pure L-[4-11C]asparagine was synthesized. Further optimization of reaction parameters, including base, metal ion source, solvent, acid component, reaction temperature and reaction time, a reliable two-step method for synthesizing L-[4- 11C]asparagine was presented; within a 45 ± 3 min (n = 5, from end-of-bombardment), the desired enantiomerically pure product was synthesized with the initial nucleophilic cyanation yield of 69 ± 4% (n = 5) and overall two-step radiochemical yield of 53 ± 2% (n = 5) based on starting [11C]HCN, and with radiochemical purity of 96 ± 2% (n = 5).},
doi = {10.1002/chem.201801029},
journal = {Chemistry - A European Journal},
number = 26,
volume = 24,
place = {United States},
year = {2018},
month = {3}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Figures / Tables:

Figure 1 Figure 1: Carbon-11 labelled radiotracers synthesized recently for plant imaging.

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Works referenced in this record:

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A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization
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    Synthese von 11 C-, 18 F-, 15 O- und 13 N-Radiotracern für die Positronenemissionstomographie
    journal, November 2008

    • Miller, Philip W.; Long, Nicholas J.; Vilar, Ramon
    • Angewandte Chemie, Vol. 120, Issue 47
    • DOI: 10.1002/ange.200800222

    A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization
    journal, June 2011

    • Donohoe, Timothy J.; Winship, Paul C. M.; Tatton, Matthew R.
    • Angewandte Chemie, Vol. 123, Issue 33
    • DOI: 10.1002/ange.201102525

    Synthesis of 11 C, 18 F, 15 O, and 13 N Radiolabels for Positron Emission Tomography
    journal, November 2008

    • Miller, Philip W.; Long, Nicholas J.; Vilar, Ramon
    • Angewandte Chemie International Edition, Vol. 47, Issue 47
    • DOI: 10.1002/anie.200800222

    A Short and Efficient Synthesis of Neodysiherbaine A by Using Catalytic Oxidative Cyclization
    journal, June 2011

    • Donohoe, Timothy J.; Winship, Paul C. M.; Tatton, Matthew R.
    • Angewandte Chemie International Edition, Vol. 50, Issue 33
    • DOI: 10.1002/anie.201102525

    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

    Rapid radiosynthesis of [11C] and [14C]azelaic, suberic, and sebacic acids for in vivo mechanistic studies of systemic acquired resistance in plants
    journal, November 2011

    • Best, Marcel; Gifford, Andrew N.; Kim, Sung Won
    • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 55, Issue 1
    • DOI: 10.1002/jlcr.1951

    Stereoselective Synthesis of Stable Isotope Labeled L-α-Amino Acids: Synthesis of L−[4−13C] and L−[3,4−13C2]Aspartic Acid
    journal, February 1992

    • Lodwig, Siegfried N.; Unkefer, Clifford J.
    • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 31, Issue 2
    • DOI: 10.1002/jlcr.2580310204

    Methods for 11 C- and 18 F-labelling of amino acids and derivatives for positron emission tomography imaging
    journal, March 2013

    • Ermert, Johannes; Coenen, Heinz H.
    • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 56, Issue 3-4
    • DOI: 10.1002/jlcr.2996

    Synthesis of [4-11C]amino acids via ring-opening of aziridine-2-carboxylates
    journal, January 2001

    • Gillings, N. M.; Gee, A. D.
    • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 44, Issue 13
    • DOI: 10.1002/jlcr.517

    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

    Investigation of SN2 [11C]cyanation for base-sensitive substrates: an improved radiosynthesis of l-[5-11C]-glutamine
    journal, December 2014


    Positron emission tomography (PET) of radiotracer uptake and distribution in living plants: methodological aspects
    journal, December 2012

    • Converse, A. K.; Ahlers, E. O.; Bryan, T. W.
    • Journal of Radioanalytical and Nuclear Chemistry, Vol. 297, Issue 2
    • DOI: 10.1007/s10967-012-2383-9

    Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis
    journal, May 1996


    Nucleophilic substitution at cyclic sulphamates—routes to NCA [18F]fluoro-analogues of MK 801
    journal, January 1989

    • Brady, F.; Luthra, S. K.; Pike, V. W.
    • International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 40, Issue 4
    • DOI: 10.1016/0883-2889(89)90225-6

    Radiosynthesis of 3-indolyl[1-11C]acetic acid for phyto-PET-imaging: An improved production procedure and formulation method
    journal, September 2014


    Nuclear physics detector technology applied to plant biology research
    journal, August 2013

    • Weisenberger, A. G.; Kross, B.; Lee, S. J.
    • Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment, Vol. 718
    • DOI: 10.1016/j.nima.2012.08.097

    Enantioselective synthesis of carbon-11 labeled l-alanine using phase transfer catalysis of Schiff bases
    journal, October 2016


    Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid
    journal, January 2015


    Working against Time:  Rapid Radiotracer Synthesis and Imaging the Human Brain
    journal, April 1997

    • Fowler, Joanna S.; Wolf, Alfred P.
    • Accounts of Chemical Research, Vol. 30, Issue 4
    • DOI: 10.1021/ar960068c

    Molecular Imaging with PET
    journal, May 2008

    • Ametamey, Simon M.; Honer, Michael; Schubiger, Pius August
    • Chemical Reviews, Vol. 108, Issue 5
    • DOI: 10.1021/cr0782426

    Synthesis of optically pure .alpha.-amino acids via salts of .alpha.-amino-.beta.-propiolactone
    journal, March 1988

    • Arnold, Lee D.; May, Robert G.; Vederas, John Christopher.
    • Journal of the American Chemical Society, Vol. 110, Issue 7
    • DOI: 10.1021/ja00215a038

    Fluoride-induced formation and ring opening of cyclic sulfamates from hydroxy triflamides. Synthetic and mechanistic studies
    journal, December 1987

    • Lyle, Terry A.; Magill, Catherine A.; Pitzenberger, Steven M.
    • Journal of the American Chemical Society, Vol. 109, Issue 25
    • DOI: 10.1021/ja00259a052

    Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S -Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis
    journal, March 2002

    • Cohen, Scott B.; Halcomb, Randall L.
    • Journal of the American Chemical Society, Vol. 124, Issue 11
    • DOI: 10.1021/ja011932l

    Chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclization with an .alpha.-amino acid
    journal, April 1993

    • Bergmeier, Stephen C.; Cobas, Agustin A.; Rapoport, Henry
    • The Journal of Organic Chemistry, Vol. 58, Issue 9
    • DOI: 10.1021/jo00061a006

    Facile and Highly Selective Conversion of Nitriles to Amides via Indirect Acid-Catalyzed Hydration Using TFA or AcOH−H 2 SO 4
    journal, March 2005

    • Moorthy, Jarugu Narasimha; Singhal, Nidhi
    • The Journal of Organic Chemistry, Vol. 70, Issue 5
    • DOI: 10.1021/jo048240a

    The synthesis of pyrimidin-4-yl substituted α-amino acids. A versatile approach from alkynyl ketones
    journal, January 1999

    • Adlington, Robert M.; Baldwin, Jack E.; Catterick, David
    • Journal of the Chemical Society, Perkin Transactions 1, Issue 8
    • DOI: 10.1039/a806741d

    Synthesis of N - t -Boc-L- a -aminoadipic Acid 1- t -Butyl 6-Ethyl Ester from L-Aspartic Acid: A New Route to L-a-Aminoadipic Acid
    journal, January 1982

    • Ramsamy, K.; Olsen, Richard K.; Emery, Thomas
    • Synthesis, Vol. 1982, Issue 01
    • DOI: 10.1055/s-1982-29692

    PET in the Diagnosis of Neuroendocrine Tumors
    journal, April 2004

    • Sundin, Anders; Eriksson, Barbro; BergstrÖM, Mats
    • Annals of the New York Academy of Sciences, Vol. 1014, Issue 1
    • DOI: 10.1196/annals.1294.027

    Application of positron emission tomography and 2-[18F]fluoro-2-deoxy-d-glucose for visualization and quantification of solute transport in plant tissues
    journal, January 2014


    Preparation and Characterization of L-[5-11C]-Glutamine for Metabolic Imaging of Tumors
    journal, December 2011