title: Stereoselective synthesis of (2S,3R)-α-hydroxy-β-amino acids (AHBAs): valinoctin A, (2S,3R)-3-amino-2-hydroxydecanoic acid, and a fluorescent-labeled (2S,3R)-AHBA.
abstract: We report the stereoselective synthesis of an alkynyl side-chain containing (2S,3R)-α-hydroxy-β-amino acid ((2S,3R)-AHBA) analogues. The Cu(I)-catalyzed reactions of (R)-glyceraldehyde acetonide and dibenzylamine with terminal alkynes provided the corresponding (2S,3R)-α-amino alcohols with good-to-excellent diastereoselectivity. Subsequent chemical transformations provided easy access to the alkynyl side-chain containing (2S,3R)-AHBAs. The utility of the methodology was demonstrated by the stereoselective synthesis of valinoctin A and (2S,3R)-3-amino-2-hydroxydecanoic acid ((2S,3R)-AHDA). Photophysical properties and cell permeability of a pyrene-labeled (2S,3R)-AHBA were also determined.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Pune , Pune, 411008 India.
authors.forename: Sharad Chandrakant
authors.initials: SC
authors.lastname: Deshmukh
authors.forename: Pinaki
authors.initials: P
authors.lastname: Talukdar
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D021542:Amino Acids, Neutral / Q000138:chemical synthesis* / Q000737:chemistry*; D003652:Decanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C481902:3-amino-2-hydroxydecanoic acid; D000596:Amino Acids; D021542:Amino Acids, Neutral; D003652:Decanoic Acids; D004151:Dipeptides; C102702:valinoctin A