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Synthesis of Isotopically Labelled L-Phenylalanine and L-Tyrosine

โœ Scribed by Jan Raap; Saskia Nieuwenhuis; Alain Creemers; Sander Hexspoor; Udo Kragl; Johan Lugtenburg

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
394 KB
Volume
1999
Category
Article
ISSN
1434-193X

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โœฆ Synopsis

A synthetic route to stable-isotope-substituted L-phenyl-synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent alanine is presented, which allows the introduction of 13 C, 15 N, and deuterium labels at any position or combination of transformation of this intermediate into the L-ฮฑ-amino acid by an enzymatic reductive amination reaction. In this positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (ี† 99% based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination ee). The method has been validated by the synthesis of [1ะˆ-13 C]-L-Phe and [2-D]-L-Phe. In addition, two methods are of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been benzonitrile and ethyl benzoate.

develop a synthetic scheme for a mono-substituted benzene

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