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Updated: Jul 3, 2026

Formation of Ordered Biomolecular Structures by the Self-assembly of Short Peptides
Published on: November 21, 2013
A pipecolic acid (Pip)-containing dipeptide, Boc-D-Ala-L-Pip-NH(i)Pr
Claude Didierjean1, Guy Boussard, André Aubry
1Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques (LCM3B), UMR nth 7036, Groupe Biocristallographie, Université Henri Poincaré, Nancy I, Faculté des Sciences, BP 239, 54506 Vandoeuvre lès Nancy Cedex, France.
Abstract:
The title dipeptide, 1-(tert-butoxycarbonyl-D-alanyl)-N-isopropyl-L-pipecolamide or Boc-D-Ala-L-Pip-NH(i)Pr (H-Pip-OH is pipecolic acid or piperidine-2-carboxylic acid), C(17)H(31)N(3)O(4), with a D-L heterochiral sequence, adopts a type II' beta-turn conformation, with all-trans amide functions, where the C-terminal amide NH group interacts with the Boc carbonyl O atom to form a classical i+3 --> i intramolecular hydrogen bond. The C(alpha) substituent takes an axial position [H(alpha) (Pip) equatorial] and the trans pipecolamide function is nearly planar.
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