Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 9 (September 2013)

organic compounds

Acta Cryst. (2013). C69, 1067-1069    [ doi:10.1107/S0108270113021914 ]

N-(L-2-Amino­penta­noyl)-L-phenyl­alanine dihydrate, a hydro­phobic dipeptide with a nonproteinogenic residue

C. H. Görbitz and V. N. Yadav

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.

Formula: C14H20N2O3·2H2O

Keywords: crystal structure; dipeptides; L-norvalyl-L-phenylalanine; nonproteinogenic residues.

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[ doi:10.1107/S0108270113021914/eg3133Isup3.cml ]
Supplementary material

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[ doi:10.1107/S0108270113021914/eg3133sup4.pdf ]
Details of the synthesis of (I)


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