Journal of Labelled Compounds and Radiopharmaceuticals

Cover image for Vol. 54 Issue 14

December 2011

Volume 54, Issue 14

Pages 819–863

  1. Research Articles

    1. Top of page
    2. Research Articles
    3. Notes
    4. Compound Index
    1. Highlighting the versatility of the Tracerlab synthesis modules. Part 2: fully automated production of [11C]-labeled radiopharmaceuticals using a Tracerlab FXC-Pro (pages 819–838)

      Xia Shao, Raphaël Hoareau, Adam C. Runkle, Louis J. M. Tluczek, Brian G. Hockley, Bradford D. Henderson and Peter J. H. Scott

      Article first published online: 20 OCT 2011 | DOI: 10.1002/jlcr.1937

      Thumbnail image of graphical abstract

      The versatility of the Tracerlab-FXC-Pro synthesis module is showcased through preparation of a range of [11C]-labeled radiopharmaceuticals. Each radiopharmaceutical is prepared using a unique radiochemical strategy. All reported syntheses are fully automated, and all products meet or exceed established quality control criteria.

    2. A gram-scale synthesis of [3,4-13C2,1α,7-2H2]cortisone (pages 839–846)

      Zizhong Li, Peter Heffner and Yumin Gong

      Article first published online: 18 OCT 2011 | DOI: 10.1002/jlcr.1938

      Thumbnail image of graphical abstract

      A gram-scale synthesis of [3,4-13C2,1α,7-2H2]cortisone from prednisone was developed. The deuterium atom at the C-1 position was introduced through a regioselective and stereoselective deuteration of the 1,2-double bond of the 1,4-diene-3-one using Wilkinson's catalyst. After the oxidative cleavage of the A-ring, two carbon-13 atoms were introduced via acetylation of an A-ring enol lactone with [1,2-13C2]acetyl chloride. The steroidal A-ring was then reconstructed to incorporate the carbon-13 atoms into the C-3 and C-4 positions. The deuterium atom at C-7 was introduced through a regioselective deuteration of the 6,7-double bond of a 4,6-diene-3-one intermediate using palladium on strontium carbonate. The M + 4 stable isotope labeled cortisone was thus prepared in ca. 4% overall yield. In addition, [3,4-13C2,1α,7-2H2]-11-dehydrocorticosterone, [3,4-13C2,1α,7-2H2]cortisol, and [3,4-13C2,1α,7-2H2]corticosterone were also prepared.

    3. Synthesis of a delta opioid agonist in [2H6], [2H4], [11C], and [14C] labeled forms (pages 847–854)

      Charles S. Elmore, Kelly Brush, Magnus Schou, William Palmer, Peter N. Dorff, Mark E. Powell, Valerie Hoesch, James E. Hall, Thomas Hudzik, Christer Halldin and Cathy L. Dantzman

      Article first published online: 18 OCT 2011 | DOI: 10.1002/jlcr.1939

      Thumbnail image of graphical abstract

      The synthesis of two H-2, a C-14, and C-11 labeled forms of a delta opioid agonist is reported. The H-2 labeled forms were prepared from [2H4]bromoethanol and [2H6]8-quinolin-8-ol. The C-14 labeled form was synthesized in one step using [14C]carbonylation, and the C-11 labeled form was prepared in two steps from 11CH3I.

  2. Notes

    1. Top of page
    2. Research Articles
    3. Notes
    4. Compound Index
    1. Synthesis of deuterium and C-13-labelled ethyl glycolate and their subsequent use in the synthesis of labelled analogues of the DNA adduct O6-carboxymethyl-2′-deoxyguanosine (pages 855–858)

      Sharon A. Moore and David E. G. Shuker

      Article first published online: 7 SEP 2011 | DOI: 10.1002/jlcr.1923

      Thumbnail image of graphical abstract

      Ethyl diazoacetate and [13C2]glycine were converted to [2H2]- and [13C2]ethyl glycolate in one-step and three-step procedures, with yields of 59% and 35%, respectively. These were then used in the synthesis of the [2H2]- and [13C2]-labelled analogues of the DNA adduct O6-carboxymethyl-2′-deoxyguanosine for use as an internal standard in liquid chromatography-mass spectrometry analyses.

  3. Compound Index

    1. Top of page
    2. Research Articles
    3. Notes
    4. Compound Index

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