title: beta-Alanine containing peptides: gamma-turns in cyclotetrapeptides.
abstract: In the present paper we describe the synthesis, purification, single-crystal x-ray analysis, solution conformational characterization, and conformational energy calculations of the cyclic tetrapeptide cyclo-(beta-Ala-L-Pro-beta-Ala-L-Val). The peptide was synthesized by classical solution methods and the cyclization of the free tetrapeptide was accomplished in good yields in diluted methylene chloride solution using N,N-dicyclohexyl-carbodiimide. The compound crystallizes in the monoclinic space group P2(1) from ethanol with two independent molecules in the unit cell. All peptide bonds are trans. The nmr molecular conformation in the acetonitrile solution as well as that derived from the molecular dynamic simulation in vacuo is quite different from those observed in the solid state and is very similar to that previously observed for the parent compound cyclo- (beta-Ala-L-Pro-beta-Ala-L-Pro).
authors: Research Center on Bioactive Peptides, CEINGE, University Federico II, Napoli, Italy.
authors: B
authors: B
authors: Di Blasio
authors: A
authors: A
authors: Lombardi
authors: G
authors: G
authors: D'Auria
authors: M
authors: M
authors: Saviano
authors: C
authors: C
authors: Isernia
authors: O
authors: O
authors: Maglio
authors: L
authors: L
authors: Paolillo
authors: C
authors: C
authors: Pedone
authors: V
authors: V
authors: Pavone
mesh_terms: D000595:Amino Acid Sequence; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation; D015091:beta-Alanine / Q000737:chemistry
chemical_list: D009842:Oligopeptides; D010456:Peptides, Cyclic; D015091:beta-Alanine