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Despite the extra functional group in the serine side chain, the crystal packing arrangement of the title compound {systematic name: (S)-3-hydroxy-2-[(S)-pyrrolidine-2-carboxamido]propanoic acid monohydrate}, C8H14N2O4·H2O, is essentially the same as observed for a series of L-Pro-L-Nop peptide hydrates, where Nop is a strictly nonpolar residue. This is rendered possible by a monoclinic P2(1) packing arrangement with Z' = 2 that deviates from orthorhombic P2(1)2(1)2(1) symmetry only for the seryl hydroxy groups, which form infinite O-H···O-H hydrogen-bonded chains along the 5.3 Å a axis. At the same time, cocrystallized water molecules form parallel water wires.


Carl Henrik Görbitz, Vitthal N Yadav. A water wire in L-prolyl-L-serine monohydrate. Acta crystallographica. Section C, Crystal structure communications. 2013 May;69(Pt 5):556-9

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PMID: 23629913

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