title: Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4R)-2-amino-4-hydroxyadipic acid (Ahad).
abstract: (2S,4R)-2-amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert-butyldimethylsilyl ether for the γ-hydroxy group of Ahad.
authors: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors: Saroj
authors: S
authors: Yadav
authors: Carol M
authors: CM
authors: Taylor
mesh_terms: D000272:Adipates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*
chemical_list: C584185:(2S)-2-amino-adipic acid; C584186:(2S,4R)-2-amino-4-hydroxyadipic acid; D000272:Adipates; D004952:Esters; D011392:Proline; D010100:Oxygen