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The synthesis of (5 R )‐ and (5 S )‐[5‐ 3 H]‐L‐ornithine
Author(s) -
Parry Ronald J.,
Ju Shyhchen,
Baker Bill J.
Publication year - 1991
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.2580290604
Subject(s) - chemistry , stereochemistry , ornithine , radiochemistry , amino acid , biochemistry , arginine
Abstract A practical synthesis of ( 5R )‐ and ( 5S )‐[5‐ 3 H]‐L‐ornithine is described. The key steps in the synthesis are the reduction of [ formyl ‐ 3 H]‐5‐hexenal with S ‐ or R ‐Alpine Borane to (1 R )‐ and (1 S )‐ [1‐ 3 H]‐5‐hexen‐1‐ol and the use of the Evans electrophilic azidation of chiral imide enolates to introduce the α‐amino group of ornithine. The stereochemistry expected for the Alpine Borane reduction was verified by NMR analysis of the camphanate ester derived from reduction of [ formyl ‐ 2 H]‐5‐hexenal with R ‐Alpine Borane.