Journal of Labelled Compounds and Radiopharmaceuticals

Cover image for Vol. 56 Issue 1

January 2013

Volume 56, Issue 1

Pages i–iv, 1–29

  1. Cover and Masthead

    1. Top of page
    2. Cover and Masthead
    3. Research Articles
    4. Protocols and Methods
    1. Editorial Board (pages i–iv)

      Article first published online: 24 JAN 2013 | DOI: 10.1002/jlcr.3026

  2. Research Articles

    1. Top of page
    2. Cover and Masthead
    3. Research Articles
    4. Protocols and Methods
    1. Preliminary studies of a novel cyclopentadienyl tricarbonyl technetium-99m fatty acid derivative for myocardical imaging (pages 1–5)

      Huahui Zeng, Huabei Zhang, Xiangxiang Wu, Fangfang Chao, Gang Yu, Liqing Zhang, Han Jiang, Hongbiao Liu, Haifeng Hou, Hongwei Zhan, Hong Zhang and Mei Tian

      Article first published online: 7 DEC 2012 | DOI: 10.1002/jlcr.2987

      Thumbnail image of graphical abstract

      Tc-99m-labeled fatty acid is very important for the evaluation of myocardial metabolism. 1 was radiolabeled by a double ligand transfer reaction between ferrocene and 99mTc. Amidated 99mTc-labeling fatty acid is beneficial to prolonging retention in myocardium.

    2. Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine (pages 6–11)

      Derek W. Barnett, Maryanne S. Refaei and Robert W. Curley Jr.

      Article first published online: 21 DEC 2012 | DOI: 10.1002/jlcr.3004

      Thumbnail image of graphical abstract

      Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position.

    3. Iodine-131 radiolabeling of poly ethylene glycol-coated gold nanorods for in vivo imaging (pages 12–16)

      Najmeh Eskandari, Kamal Yavari, Mohammad Outokesh, Sodeh Sadjadi and Seyed Javad Ahmadi

      Article first published online: 28 DEC 2012 | DOI: 10.1002/jlcr.3006

      Thumbnail image of graphical abstract

      We have developed a rapid and simple method for radiolabeling of gold rods with iodine-131 in order to track in vivo tissue uptake of gold nanorods after systemic administration by biodistribution analysis and γ-imaging.

    4. A modern approach to the synthesis of 2-(4-chlorophenyl)[2- 14C]thiazol-4-ylacetic acid ([14C] fenclozic acid) and its acyl glucuronide metabolite (pages 17–21)

      David A. Killick and Nick Bushby

      Article first published online: 11 JAN 2013 | DOI: 10.1002/jlcr.2985

      Thumbnail image of graphical abstract

      [14C]Fenclozic acid and its key acyl glucuronide metabolite, the 1-β-O-acyl glucuronide were prepared from labelled potassium cyanide. [14C]Fenclozic acid had previously been prepared in the 1960s, however in this paper we describe a shorter synthesis that avoids or reduces some of the inherent hazards present in the original synthesis.

    5. Expeditious syntheses of stable and radioactive isotope-labeled anticonvulsant agent, JNJ-26990990, and its metabolites (pages 22–26)

      Ronghui Lin, Larry E. Weaner, David C. Hoerr, Rhys Salter and Yong Gong

      Article first published online: 10 JAN 2013 | DOI: 10.1002/jlcr.3013

      Thumbnail image of graphical abstract

      Syntheses of stable and radioactive isotope-labeled anticonvulsant agent, JNJ-26990990 (N-(benzo[b]thien-3-ylmethyl)-sulfamide), and its metabolites are described. [13C15N]Benzo[b]thiophene-3-carbonitrile was first prepared by coupling of 3-bromo-benzo[b]thiophene with [13C15N]-copper cyanide. The resultant [13C15N]benzo[b]thiophene-3-carbonitrile obtained was reduced with lithium aluminum deuteride to give [13CD215N]benzo[b]thiophen-3-yl-methylamine; which was then coupled with sulfamide to afford [13CD215N]-N-(benzo[b]thien-3-ylmethyl)-sulfamide (1), the stable isotope-labeled compound with four stable isotope atoms. Direct oxidation of [13CD215N]-N-(benzo[b]thien-3-ylmethyl)-sulfamide with hydrogen peroxide and peracetic acid gave the stable isotope-labeled sulfoxide and sulfone metabolites correspondingly. On the other hand, radioactive 14C-labeled N-(benzo[b]thien-3-ylmethyl)-sulfamide (2) was prepared conveniently by sequential coupling of 3-bromo-benzo[b]thiophene with [14C]-copper cyanide, reduction of the carbonitrile to carboxaldehyde, and reductive amination with sulfamide.

  3. Protocols and Methods

    1. Top of page
    2. Cover and Masthead
    3. Research Articles
    4. Protocols and Methods
    1. Gram-scale synthesis and efficient purification of 13C-labeled levoglucosan from 13C glucose (pages 27–29)

      Lisa Alexander, Caroline Hoyt, Ryszard Michalczyk, Ruilian Wu, Dave L. Thorn and L. A. ‘Pete’ Silks

      Article first published online: 14 NOV 2012 | DOI: 10.1002/jlcr.2978

      Thumbnail image of graphical abstract

      13C-Labeled levoglucosan has been synthesized and purified in good yield, and on the gram scale in one step from commercially available 13C glucose. This one-step protocol uses 2-chloro-1,3-dimethylimidazolinium chloride that serves to selectively activate the anomeric carbon group toward substitution reactions. The labeled glucose is then smoothly converted to the anhydroglucose. Purification is efficiently achieved on large scale by chromatography on silica gel.

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