The isolation of γ-hydroxyarginine, as its lactone, from seeds of Vicia sativa, and the identification of γ-hydroxyornithine as a naturally occurring amino acid

Natural Guanidino Compounds

“…The hydroxy compound was obtained from the seeds of L. tingitanus (Bell, 1964). The comparative distribution of guanidino compounds in the seeds of two genus of the Papilionoideae, Lathyrus and Vicia, exhibits interesting features (Bell and Tirimanna, 1964). For example, the genus Lathyrus stores predominantly the C7 amino acids homoarginine, y-hydroxyhomoarginine and the related compound lathyrine, while the genus Vicia stores relatively high concentrations of canavanine and of the C6 amino acids arginine and y-hydroxyarginine.…”

Highly Efficient Chiral-Pool Synthesis of (2S,4R)-4-Hydroxyornithine

“…(2 S ,4 R )-4-Hydroxyornithine ( 1 ) is a nonproteinogenic amino acid that is widely found in nature. For example, it is a component of marine organism and plants, as well as a constituent of a number of peptide natural products, such as the antifungal lipopeptides echinocandin and pneumocandin, the K 582 type antibiotics, and the biphenomycin antibiotics . The interest in (2 S ,4 R )-4-hydroxyornithine ( 1 ) is documented in a variety of synthetic approaches previously described in the literature.…”

Synthesis and application in peptide chemistry of amino acids possessing an optically active selenohomocysteine skeleton

“…Found: C, 60.9; H, 5.99; N, 8.56. N-Carbobenzoxy-L-selenomethionine p-Nitrobenzyl Ester (15). -Sodium (0.065 g) was dissolved in ethanol (5 ml) in a threenecked flask equipped with two dropping funnels, a magnetic stirrer, an inlet for passing the gases through the solution, and an outlet connected to a trap containing a 10% solution of NaOH, Hydrogen selenide from a tank mixed with a slow stream of hydrogen was passed under exclusion of air through the solution of sodium ethoxide.…”