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

Abstract

SummaryA directed manipulation of the functional groups at C3 and C4 of D-glucose was demonstrated to synthesize naturally occurring (2S,3R)-α-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.

Study of the β-oxygen effect in the Barton–McCombie reaction for the total synthesis of (4R,5R)-4-hydroxy-γ-decalactone (Japanese orange fly lactone): a carbohydrate based approach

“…13 The olen was reduced with Pd/C in 93% yield to obtain the saturated derivative (11). 14 Aer being treated with Amberlite IR-120 H + in methanol, the saturated derivative yielded 86% of a mixture of methyl glycosides (12). 15 The anomers formed in the above step was separated by Biotage chromatography and isolated both the anomeric compounds 12a (42%) & 12b (44%) and been characterized with the support of 2D NMR spectroscopic studies.…”

Cross-Aldol Reaction of Activated Carbonyls with Nitrosocarbonyl Intermediates: Stereoselective Synthesis toward α-Hydroxy-β-amino Esters and Amides

“…α-Hydroxy-β-amino carbonyls represent an increasingly demanding field of research, as molecules embracing this framework are ubiquitous in pharmaceutically active compounds and complex natural products . Prominent examples include the potent aminopeptidase inhibitor bestatin, the HIV protease inhibitor KNI-272, and the blockbuster anticancer drug Taxol (Figure ).…”