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4‐Naphthylmethyl Proline Forms a Channel Structure
Author(s) -
Foletti Carlotta,
Trapp Nils,
Loosli Simon,
Lewandowski Bartosz,
Wennemers Helma
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900052
Subject(s) - chemistry , proline , hydrogen bond , amphiphile , amino acid , carboxylate , derivative (finance) , stereochemistry , molecule , organic chemistry , biochemistry , copolymer , polymer , economics , financial economics
Proline and proline derivatives are useful tools to control the structural properties of peptides and proteins, and thereby modulate numerous processes. Here, we show that proline derivatives can have unique structural properties in the solid state by presenting the crystal structure of zwitterionic (2 S ,4 S )/(2 S ,4 R )‐4‐[(naphthalen‐2‐yl)methyl]proline (H‐Nap‐OH). This amphiphilic proline derivative forms a columnar structure around large hydrophilic and small hydrophobic channels with diameters of 9 Å and 4 Å, respectively. We show that this architecture, which is unprecedented for amino acids, results from the combination of a hydrogen bond network between the ammonium and carboxylate moieties and π – π as well as CH– π interactions between the aromatic moieties.