Crystal structures of natural amino acid perhydrates

Petr V. Prikhodchenko, Alexander G. Medvedev, Tatiana A. Tripol'Skaya, Andrei V. Churakov, Yitzhak Wolanov, Judith A.K. Howard, Ovadia Lev

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

The structures of various natural amino acid hydrogen peroxide solvates are presented. All "active" hydrogen atoms (amino, hydroxy, peroxy, and water) in the studied amino acid perhydrates are involved in hydrogen bonding. Peroxide molecules form at least two donor hydrogen bonds. In the most common case, the H2O2 molecule is engaged in four hydrogen bonds (two donors with -CO2- groups and two acceptors with -NH3+ groups). In peroxosolvates of amino acids bearing hydrocarbon side-chains, double layers were observed. These bilayers are hydrophilic inside, while their outer surfaces are hydrophobic. It was found that donor hydrogen bonds formed by hydrogen peroxide in amino acid perhydrates are significantly stronger than those formed by water molecules in amino acid hydrates.

Original languageEnglish
Pages (from-to)2399-2407
Number of pages9
JournalCrystEngComm
Volume13
Issue number7
DOIs
StatePublished - 7 Apr 2011

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