Catalytic reduction in the synthesis of tritiated (6R) and (6S) 5, 10-dideaza-5,6,7,8-tetrahydrofolate

✍ Scribed by Ann D. Cross; H. Morimoto; P. G. Williams; G. P. Beardsley

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: French
• Weight: 409 KB
• Volume: 29
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580290704

✦ Synopsis

Abstract

[^3^H] 5,10‐dideaza‐5,6,7,8‐tetrahydrofolate, DDATHF, was obtained by a two step process. First, 2n[^3^H~2~O] was produced in the reaction flask containing m[^1^HAc] by the reduction of n[PtO~2~] with ^3^H~2~, so that a 1[^3^H^+^]:18[^3^H^+^ + ^1^H^+^] ratio of solvent protic species in theory resulted. Secondly, subsequently added diethyl‐2‐acetyl‐5,10‐dideaza‐9,10‐didehydrofolate was reduced in this tritium labeled solvent with the pre‐reduced Adams catalyst and additional carrier free tritium gas which was introduced to a pressure of 722 torr. The resulting (6R) and (6S) [^3^H] diastereomers were individually isolated. Each had a specific activity of 11.2 Ci/mmol, and the locations of the incorporated tritium atoms were completely determined by ^1^H decoupled 320 MHz ^3^H NMR by comparison with the 300 and 500 MHz ^1^H NMR spectra of [^1^H] (6S) DDATHF, [^1^H] (6R) DDATHF, and [5‐^2^H (50% ^2^H), 6‐^2^H (100% ^2^H), 7‐^2^H (50% ^2^H), 9‐^2^H (50% ^2^H), 10‐^2^H (50% ^2^H)] (6RS) DDATHF.