Stereocontrolled synthesis of peptide bond isosteres.
Absolute stereochemical control is employed in the synthesis of isosteres for dipeptide subunits (1; see Fig. 1) in which the amide linkage has been replaced by a trans carbon-carbon double bond. The synthesis affords access to the four stereoisomers of 1 in which R and R' = CH3, including the isostere for D-alanine-D-alanine (D-Ala-D-Ala), 2.
Whitesell
J K
JK
Department of Chemistry, University of Texas, Austin 78712.
Lawrence
R M
RM
D000595:Amino Acid Sequence; D007202:Indicators and Reagents; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010455:Peptides