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Synthesis and conformational preferences in solution and crystalline states of an aza-tripeptide

✍ Scribed by Christine Hemmerlin; Manh Thong Cung; Guy Boussard

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
145 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The aza-tripeptide Boc-Ala-AzPip-Ala-NHiPr (AzPip: 2-aza pipecolyl residue) was synthesized in seven steps using preferentially the diisopropylcarbodiimide/1-hydroxy-7-aza-benzotriazole (DIPCDI/AtOH) coupling method and via the Boc-AzPip-OBzl pivotal intermediate. Its crystal molecular structure is characterized by the presence of a bVI-like turn around the N-terminal Ala-AzPip sequence and stabilized by two intramolecular hydrogen bonds sharing the same (Boc)CO carbonyl acceptor. In solution (chloroform, DMSO), two isomers are in equilibrium, one of them resembling the stereoisomer found in the crystal, the other being unfolded, but keeping the cis-isomerism of the Ala-AzPip bond and the pronounced degree of pyramidicity of the axial 2-amide N a nitrogen atom.

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