Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

• Rajendra S. Rohokale and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2014, 10, 667–671, doi:10.3762/bjoc.10.59

• -hydroxy-β-aminodecanoic acid (AHDA, 2a) and its enantiomer 2b. The enantiomer of 2a is the N-terminal part of the natural linear pentapeptide microginin, which is used as an antihypertensive agent. Keywords: AHDA; carbohydrate; chiron approach; enantioselective; natural products; non-proteinogenic amino

• acid; Introduction Microginin 1 (Figure 1), isolated from the cyanobacterium Microcystis aeruginosa, is a linear pentapeptide consisting of L-Tyr-L-N-Me-Tyr-L-Val-L-Ala and (2S,3R)-α-hydroxy-β-aminodecanoic acid ((2S,3R)-AHDA, 2a) [1]. Microginin is used as a hypertensive agent based on its biological

• activity against angiotensin converting enzyme, which is responsible for the vasoconstriction of blood vessels [2][3][4]. Amongst different amino acids present in microginin, (2S,3R)-AHDA (2a) is a non-proteinogenic natural amino acid attached at the N-terminal part of the peptide chain. The α-hydroxy-β