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1998•Journal of Labelled Compounds and RadiopharmaceuticalsRequires access

Synthesis of optically pure (D)-phenyl[3-14C]alanine

E. Koltai, A. Alexin, Gy. Rutkai, Éva Tóth-Sarudy

Open publisher page 3 citations

Abstract

Lithium aluminium hydride reduction of methyl [7-14C]benzoate gave [7-14C]benzyl alcohol which was transformed (HBr, H2SO4) to [7-14C]benzyl bromide. The latter was reacted with lithium N-(bis-methylthiomethylenimino)-acetyl-(2R)-bornane-10,2-sultam (Oppolzer chiral synthon) followed by hydrochloric acid then lithium hydroxide hydrolysis and chromatography on a Dowex 50 column to give (D)-phenyl[3-14C]alanine with 40% overall yield. The molar activity was higher than 50 mCi/mmol and e.e.>99% as measured by the Marfey method and a modified Marfey method with TLC scanning. The latter method is suitable for the measurement of the optical purity of any amino acid. Copyright © 1998 John Wiley & Sons, Ltd.

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What this paper is about

Lithium aluminium hydride reduction of methyl [7-14C]benzoate gave [7-14C]benzyl alcohol which was transformed (HBr, H2SO4) to [7-14C]benzyl bromide. The latter was reacted with lithium N-(bis-methylthiomethylenimino)-acetyl-(2R)-bornane-10,2-sultam (Oppolzer chiral synthon) followed by hydrochloric acid then lithium hydroxide hydrolysis and chromatography on a Dowex 50 column to give (D)-phenyl[3-14C]alanine with 40% overall yield. The molar activity was higher than 50 mCi/mmol and e.e.>99% as measured by the Marfey method and a modified Marfey method with TLC scanning. The latter method is suitable for the measurement of the optical purity of any amino acid. Copyright © 1998 John Wiley & Sons, Ltd.

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Available abstract

Lithium aluminium hydride reduction of methyl [7-14C]benzoate gave [7-14C]benzyl alcohol which was transformed (HBr, H2SO4) to [7-14C]benzyl bromide. The latter was reacted with lithium N-(bis-methylthiomethylenimino)-acetyl-(2R)-bornane-10,2-sultam (Oppolzer chiral synthon) followed by hydrochloric acid then lithium hydroxide hydrolysis and chromatography on a Dowex 50 column to give (D)-phenyl[3-14C]alanine with 40% overall yield. The molar activity was higher than 50 mCi/mmol and e.e.>99% as measured by the Marfey method and a modified Marfey method with TLC scanning. The latter method is suitable for the measurement of the optical purity of any amino acid. Copyright © 1998 John Wiley & Sons, Ltd.

Key concepts: Chemistry, Synthon, Lithium aluminium hydride, Bromide, Hydrolysis, Lithium (medication), Yield (engineering), Alanine

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