AI Article Synopsis
- The study explores the differentiation of five pairs of diastereomers (specifically beta-amino acids and norbornane/norbornene amino acids) using a kinetic method with metal-bound trimeric complexes.
- This approach is novel, as it allows for the first-time kinetic differentiation of these types of diastereomers.
- Results indicate that selectivity improved with the rigidity of the molecular structures, and variations in metal ions (Cu(2+) and Ni(2+)) influenced the selectivity outcomes.
Article Abstract
Stereochemical differentiation of five diastereomeric pairs of beta-amino acids, di-endo- and di-exo-2,3-disubstituted norbornane and norbornene amino acids, cis- and trans-2-aminocyclohexane-, 2-amino-4-cyclohexene-, and 2-aminocyclopentanecarboxylic acids, was investigated via the kinetic method with metal-bound trimeric complexes. This is the first time that diastereomers (di-endo/di-exo and cis/trans) have been differentiated with metal-bound trimeric complexes and the kinetic method. Moreover, determination of diastereochemical excess by the kinetic method was applied to norbornane beta-amino acids and cyclopentane beta-amino acids. Experiments showed that a remarkable differentiation of the studied diastereomers was achieved. It was observed that better selectivity values correlated to more rigid structures. The reference compounds for the studied beta-amino acids varied from alpha-amino acids to some beta-amino acids. In addition, variation of the metal ion (Cu(2+) and Ni(2+)) had some role in the selectivity values obtained. Ab initio and hybrid density functional theory calculations were performed to clarify the results obtained by mass spectrometry.
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| http://dx.doi.org/10.1016/j.jasms.2008.09.018 | DOI Listing |
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