Medicinal Chemistry of α‐Hydroxy‐β‐Amino Acids

Comparison of the Separation Performances of Cinchona Alkaloid-Based Zwitterionic Stationary Phases in the Enantioseparation of β2- and β3-Amino Acids

“…). β -Amino acids are applied in the synthesis of heterocyclic derivatives with wide structural diversity, and a rapidly growing class of oligomeric peptides with considerable biological and catalytic properties [1,2,3,4,5]. The newly developed enantioselective syntheses of β -amino acids [5,6,7,8] require analytical methods for a check on the enantiopurity of the final products.…”

High anti Diastereoselectivity in a Tandem Oxyhomologation–Coupling Protocol for the Preparation of Amides and Peptides Incorporating α-Hydroxy β-Amino Acids

“…α-Hydroxy β-amino acids are an important class of molecules in both natural products and medicinal chemistry . The two carbons bearing the vicinal amino alcohol moiety are often stereogenic, leading to the existence of two diastereoisomeric forms.…”

“…α-Hydroxy β-amino acids are an important class of molecules in both natural products 1 and medicinal chemistry. 2 The two carbons bearing the vicinal amino alcohol moiety are often stereogenic, leading to the existence of two diastereoisomeric forms. Derivatives with an anti relative configuration appear in both linear and cyclic natural peptides (Figure 1), such as microginin 674 3 and perthamide C. 4 Small synthetic peptides incorporating anti α-hydroxy β-amino acids are important constituents of protease inhibitors, and particular attention has been given to (2S,3S)-allophenylnorstatin derivatives (Figure 1): AG-001859 was in preclinical development for anti-HIV activity, 5 and was recently considered as a SARS-CoV2 antiviral; 6 KMI-1027 acts as a BACE-1 inhibitor 7 and has potential for Alzheimer's disease treatment; 8 KNI-272 is an HIV-1 protease inhibitor, 9 and reduces HIV-related neurotoxicity.…”