Syntheses of the (±)‐, (+)‐, and (−)‐Forms of 2‐Amino‐3‐(8‐hydroxyquinolin‐3‐yl)propanoic Acid (8HQ‐3Ala) from a Common Dehydroamino Acid Methyl Ester Precursor
Abstract:The (±)‐, (+)‐ and (−)‐forms of 2‐amino‐3‐(8‐hydroxyquinolin‐3‐yl)‐propanoic acid (1 or 8HQ‐3Ala) have been prepared from o‐methoxyacetanilide (2). A combination of Vilsmeier‐Haack, Erlenmeyer‐Plöchl and methanolysis reactions was used to convert compound 2 into the Z‐configured dehydroamino acid derivative 5. Catalytic hydrogenation of the latter compound then gave, after reductive dechlorination and demethylation steps, compound (±)‐1. Asymmetric hydrogenation of compound 5 using a rhodium precatalyst and an… Show more
The ability for amino acid residues to bind metals underpins the functions of metalloproteins to conduct a plethora of critical processes in living organisms as well as unnatural applications in...
The ability for amino acid residues to bind metals underpins the functions of metalloproteins to conduct a plethora of critical processes in living organisms as well as unnatural applications in...
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