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 1 H and 13 C 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.