Synthesis and Stereochemistry of Hypusine, a New Amino Acid in Bovine Brain

Article abstract of DOI:10.1246/bcsj.55.899

Hypusine, a new basic amino acid occurring in the homogenate of bovine brain tissue, was synthesized to determine the absolute structure.N^α-Benzyloxycarbonyl-L-lysine benzyl ester was coupled with (S)- or (R)-4-benzyloxycarbonylamino-1-bromo-2-butanol derived from L- or D-malic acid, respectively.The products were deprotected by catalytic dehydrogenation.One of the synthetic compounds, i.e., (2S,9R)-2,11-diamino-9-hydroxy-7-azaundecanoic acid, was completely identical with natural hypusine in all respects.