title: N-(L-2-aminopentanoyl)-L-phenylalanine dihydrate, a hydrophobic dipeptide with a nonproteinogenic residue.
abstract: The title dipeptide, better known as L-norvalyl-L-phenylalanine {systematic name: (S)-2-[(S)-2-aminopentanamido]-3-phenylpropanoic acid dihydrate}, C14H20N2O3·2H2O, has a nonproteinogenic N-terminal residue. In the solid state, it takes on a molecular conformation typical for one of the three classes of nanoporous dipeptides, but like two related compounds with a hydrophobic N-terminal residue and a C-terminal L-phenylalanine, it fails to form channels or pores. Instead, the crystal structure is divided into distinct hydrophobic and hydrophilic layers, the latter encompassing cocrystallized water molecules connecting the charged N- and C-terminal groups.
authors.affiliation: Department of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway. c.h.gorbitz@kjemi.uio.no
authors.forename: Carl Henrik
authors.initials: CH
authors.lastname: Görbitz
authors.forename: Vitthal N
authors.initials: VN
authors.lastname: Yadav
mesh_terms: D018360:Crystallography, X-Ray; D004151:Dipeptides / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D010666:Phenylpropionates / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: C587348:(S)-2-((S)-2-aminopentanamido)-3-phenylpropanoic acid dihydrate; D004151:Dipeptides; C587347:N-(L-2-aminopentanoyl)-L-phenylalanine dihydrate; D010666:Phenylpropionates; D014867:Water; D010649:Phenylalanine
keywords: crystal structure; dipeptides; l-norvalyl-l-phenylalanine; nonproteinogenic residues