Mixed conformation in Cα,α‐disubstituted tripeptides: X‐ray crystal structures of Z‐Aib‐Dph‐Gly‐Ome and Bz‐Dph‐Dph‐Gly‐Ome

We report here the synthesis and molecular structure in the solid state of fully protected tripeptides containing Cα,α‐diphenylglycine (Dph), namely Z‐Aib‐Dph‐Gly‐OMe (Aib: Cα,α‐dimethylgrycine) and Bz‐Dph‐Dph‐Gly‐OMe. The molecular conformation around the Dph residue, containing two bulky substituents, is fully extended, while the Aib residue, containing two smaller groups on the Cα atom, adopts the typical 310/α‐helical conformation. Gly residues, without substituents on the Cα atom, show different conformational preferences. Each residue seems to behave, from a conformational point of view, independently from the presence of the other residues, and thus mixed local conformations (folded and extended) are present in the crystals. The nonconventional peptide synthesis, using the Ugi reaction, is also reported. © 1994 John Wiley & Sons, Inc. Copyright © 1994 John Wiley & Sons, Inc.