Synthesis and conformation of Gly-Gly dipeptides constrained with phenylalanine-like aminocaproic acid linkers.
[structure: see text] The constraint of dipeptides with linkers derived from 6-aminocaproic acid (Aca) is a useful means of constructing a beta-turn peptidomimetic. The extension of this concept to the mimicry of a tripeptide entails the incorporation of a side chain moiety on either end of the Aca chain. The synthesis and conformational analysis of two exemplary compounds is discussed.
MacDonald
M
M
Department of Medicinal Chemistry, University of Kansas, Lawrence , 66045-2506, USA.
Vander Velde
D
D
Aubé
J
J
D015119:Aminocaproic Acid / Q000737:chemistry; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D005998:Glycine / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D017433:Protein Structure, Secondary
D004151:Dipeptides; D005998:Glycine; D015119:Aminocaproic Acid