Asymmetric synthesis of the N-terminal component of microginin: (2S,3R)-3-amino-2-hydroxydecanoic acid, its (2R,3R)-epimer and (3R)-3-aminodecanoic acid
Bunnage ME., Burke AJ., Davies SG., Goodwin CJ.
3-Amino-2-hydroxydecanoic acid (AHDA) is a novel amino acid which has been suggested as the N-terminal component of the recently isolated angiotensin-converting enzyme inhibitor microginin. The naturally occurring amino acid was found to possess syn relative stereochemistry and (2S,3R) absolute stereochemistry when the reported 1H and 13C nmr spectroscopic data and the CD data were compared to the spectroscopic data for synthetic (2R,3R)- and (2S,3R)-AHDA. These studies complete the stereochemical assignment of microginin. © 1994.