Journal of Labelled Compounds and Radiopharmaceuticals

Nagamura, Satoro; Kinugawa, Masahiko; Ogasa, Takehiro; Saito, Hiromitsu

doi: 10.1002/(SICI)1099-1344(199706)39:6<471::AID-JLCR991>3.0.CO;2-Kpmid: N/A

The synthesis of (3H)KW‐2189, 2, a novel active antitumor antibiotic, is described. The key intermediate, 6, in the synthesis, was synthesized in four steps from duocarmycin B2 (1). Treatment of 6 with (3H)methyl iodide in the presence of NaHCO3 in MeOH‐Me2CO (1:1) afforded the (3H)KW‐2189 with highly specific activity of 86.4 Ci/mmol. © 1997 John Wiley & Sons, Ltd.

Matthews, Lee; Ellis, Martin K; Cullis, Paul N; Farmer, Peter B

doi: 10.1002/(SICI)1099-1344(199706)39:6<479::AID-JLCR993>3.0.CO;2-6pmid: N/A

(R)‐(2,3,4,5,6‐Pentadeuterophenyl)oxirane, 5 was synthesized with an overall yield of 6.3% from benzene‐d6. Friedel‐Crafts acylation of benzene‐d6 with methyl oxalylchloride gave methyl 2‐oxo‐2‐(2,3,4,5,6‐pentadeuterophenyl)acetate, 1 that was chirally reduced (Saccharomyces cerevisiae) to methyl (R)‐2‐hydroxy‐2‐(2,3,4,5,6‐pentadeuterophenyl)acetate (methyl (R)‐d5‐mandelic acid), 2. Reduction of 2 with lithium aluminium hydride gave (R)‐(2,3,4,5,6‐pentadeuterophenyl)ethane‐1,2‐diol, 3. Tosylation of 3 and subsequent treatment with potassium hydroxide assisted cyclisation to 5. © 1997 John Wiley & Sons, Ltd.

Abbadi, Mehdi; Mathieu, Jean‐Paul; Morin, Christophe

doi: 10.1002/(SICI)1099-1344(199706)39:6<487::AID-JLCR994>3.0.CO;2-2pmid: N/A

A preparation of a D‐glucose analogue in which the 4‐hydroxyl group can be replaced by radioactive iodine is presented. © 1997 John Wiley & Sons, Ltd.

Roscher, René; Schreier, Peter; Schwab, Wilfried

doi: 10.1002/(SICI)1099-1344(199706)39:6<493::AID-JLCR990>3.0.CO;2-Fpmid: N/A

A convenient one‐step synthesis of 14C‐labelled 2,5‐dimethyl‐4‐hydroxy‐3(2H)‐furanone (furaneol) was accomplished by a piperidine acetate catalyzed Maillard‐type reaction of commercially available fucose L‐(1‐14C). This important aroma compound found in strawberry fruits, obtained in ≥ 90 % radiochemical purity, should prove useful in in‐vivo metabolism studies. © 1997 John Wiley & Sons, Ltd.

Held, Pierre; Heck, Marie‐Pierre; Iyer, Jaya; Gronemeyer, Hinrich; Lebeau, Luc; Mioskowski, Charles

doi: 10.1002/(SICI)1099-1344(199706)39:6<501::AID-JLCR995>3.0.CO;2-Spmid: N/A

Synthesis of 4‐(2‐(5,5,8,8‐tetramethyl‐5,6,7,8‐tetrahydro‐naphthalen‐2‐yl)‐(1,3)dioxolan‐2‐yl)‐benzoic acid or SR11237, a specific ligand of Retinoid X Receptors, is described in a 3H‐labelled version. The labelled retinoid was prepared in 5 steps and tritium was introduced through a final reduction of an aromatic dihalide moiety with 3H2. © 1997 John Wiley & Sons, Ltd.

Neu, Henrik; Kihlberg, Tor; Långström, Bengt

doi: 10.1002/(SICI)1099-1344(199706)39:6<509::AID-JLCR996>3.0.CO;2-Hpmid: N/A

A method for the preparation of saturated fatty acids 11C (13C)‐labelled in the ω‐methyl position is described. A highly reactive zerovalent copper complex was prepared from lithium naphtalenide reduced lithium(2‐thienyl)iodocuprate. The labelling precursors were obtained by addition of tert‐butyl ω‐iodocarboxylates to the organocuprate and these were reacted with (11C)methyl iodide to form 11C‐labelled, protected intermediates. The tert‐butyl ester protecting group was rapidly removed with trifluoroacetic acid, affording fatty acids 11C‐labelled in the ω‐methyl position. A solid phase extraction method was developed and preceded final HPLC purification. In a typical run starting with 2.75 GBq of (11C)methyl iodide, 375 MBq (66%) (16‐11C)palmitic acid was obtained within 46 min from the end of the radionuclide production. © 1997 John Wiley & Sons, Ltd.

Westerberg, Göran; Långström, Bengt

doi: 10.1002/(SICI)1099-1344(199706)39:6<525::AID-JLCR998>3.0.CO;2-9pmid: N/A

An efficient and fully automated one‐pot method for the synthesis of 3‐iodobenzyl (11C)guanidine ((11C)MIBG) was developed. Starting from (11C)cyanogen bromide, (11C)MIBG was obtained in 62 % radiochemical yield and a radiochemical purity higher than 98 % via the intermediate 3‐iodobenzyl (11C)cyana/μmol (130 GBq/μmol) at the end of synthesis. © 1997 John Wiley & Sons, Ltd.

Tsikas, Dimitrios; Schwedhelm, Edzard; Gutzki, Frank‐Mathias; Jahn, Olaf; Fakistas, Panagiotis; Frölich, Jürgen C.

doi: 10.1002/(SICI)1099-1344(199706)39:6<531::AID-JLCR3>3.0.CO;2-Opmid: N/A

8‐epi‐Prostaglandin F2α (8‐epi‐PGF2α) is an endogenous potent vasoconstrictor, non‐cyclooxygenase‐derived prostanoid which may be suitable as an index of oxidative stress in living organisms. For quantitative determination of 8‐epi‐PGF2α in biological fluids we describe here the one‐step enzymatic synthesis of (1,1‐18O2)‐8‐epi‐PGF2α starting from commercially available unlabeled 8‐epi‐PGF2α, H218O and an unspecific porcine liver esterase. The isolated and purified reaction product was found to contain 80.3 % of (1,1‐18O2)‐8‐epi‐PGF2α, 17.7% of (1,1‐18O16O)‐8‐epi‐PGF2α and only 2% of unlabeled 8‐epi‐PGF2α. (1,1‐18O2)‐8‐epi‐PGF2α is demonstrated to be a suited internal standard for quantitative determination of 8‐epi‐PGF2α in human urine by GC‐MS/MS. In 5‐ml aliquots of human urine samples from spontaneous micturation on different days, 8‐epi‐PGF2α was found to be present at concentrations of 300 and 490 pq/mg creatinine, respectively. © 1997 John Wiley & Sons, Ltd.