Chirally directed formation of nanometer-scale proline clusters

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Ion mobility measurements, combined with molecular mechanics simulations, are used to study enantiopure and racemic proline clusters formed by electrospray ionization. Broad distributions of cluster sizes and charge states are observed, ranging from clusters containing only a few proline units to clusters that contain more than 100 proline units (i.e., protonated clusters of the form [xPro + nH](n+) with x = 1 to > 100 and n = 1 - 7). As the sizes of clusters increase, there is direct evidence for nanometer scale, chirally induced organization into specific structures. For n = 4 and 5, enantiopure clusters of similar to 50 to 100 prolines assemble into structures that are more elongated than the most compact structure that is observed from the racemic proline clusters. A molecular analogue, cis-4-hydroxy-proline, displays significantly different behavior, indicating that in addition to the rigidity of the side chain ring, intermolecular interactions are important in the formation of chirally directed clusters. This is the first case in which assemblies of chirally selective elongated structures are observed in this size range of amino acid clusters. Relationships between enantiopurity, cluster shape, and overall energetics are discussed.
Publisher
AMER CHEMICAL SOC
Issue Date
2006-08
Language
English
Article Type
Article
Keywords

IONIZATION MASS-SPECTROMETRY; ION MOBILITY SPECTROMETRY; MAGIC NUMBER CLUSTERS; GAS-PHASE; ELECTROSPRAY-IONIZATION; SERINE OCTAMER; PLASMA CHROMATOGRAPHY; MOLECULAR-DYNAMICS; FUNNEL INTERFACE; ACID

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.128, no.33, pp.10833 - 10839

ISSN
0002-7863
DOI
10.1021/ja0622711
URI
http://hdl.handle.net/10203/203340
Appears in Collection
CH-Journal Papers(저널논문)
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