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The enantiospecific synthesis of [5‐ 2 H]‐epi‐shikimic acid and of (6R) [6‐ 2 H]‐, (6S) [6‐ 2 H]‐ and [6‐ 2 H 2 ] shikimic acid
Author(s) -
Zamir Lolita O.,
Nguyen CongDanh,
Li Shu Wen,
Nikolakakis Anastasia,
Sauriol Françoise
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580311107
Subject(s) - shikimic acid , chemistry , enantioselective synthesis , stereospecificity , stereochemistry , ketone , shikimate pathway , organic chemistry , biosynthesis , enzyme , catalysis
The enantioselective synthesis of [5‐ 2 H]‐5‐epi‐shikimic acid starting from commercially available L ‐shikimic acid has been accomplished in this work. The introduction of the stable isotope was facilitated by an enzymic reduction of a ketone. An interesting stereospecific enolisation was also observed during this reaction resulting in partial deuteration of the 6‐equatorial position. In addition, the enantioselective syntheses of methyl (6R) [6‐ 2 H]‐, and (6 S ) [6‐ 2 H] shikimate are described. The procedure is an adaptation of a reported (1) enantiospecific synthesis of shikimic acid, with the inclusion of an enzymic reduction step.