Synthesis, self-association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 50; no. 13; pp. 1215 - 1223
• Main Authors: Kuhnert, Nikolai, Le-Gresley, Adam, Nicolau, Daniel C., Lopez-Periago, Ana
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.11.2007; Wiley
• Subjects: Biochemical Research Methods; Biochemistry & Molecular Biology; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; chiral recognition; deuterium labeling; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Life Sciences & Biomedicine; macrocyclic chemistry; mass spectrometry; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; supramolecular chemistry; TRIANGLIMINE; deuterium labeling; SERINE; macrocyclic chemistry; mass spectrometry; chiral recognition; ISOTOPOMERS; supramolecular chemistry; EFFICIENT PARALLEL RESOLUTION; SUPRAMOLECULAR CHIRALITY; Isotope labelling; Nitrogen heterocycle; Hydrogen Isotopes; Imine; Deuteriation; Chiral recognition; Electrospray; Macrocycle; Self association; Ion trap; Supramolecular structure; Chemical synthesis; Mass spectrometry
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/jlcr.1449

The synthesis and self‐association of chiral isotopically labeled trianglamine macrocycles under electrospray mass spectrometer conditions in an ion trap are described. A moderate diastereoselectivity in the self‐association process was observed providing a synthetic model system for the investigation of chiral self‐association in the gas phase. The first non‐covalently bound dimer exclusively bonded through aromatic–aromatic interactions was observed in the gas phase. Evidence for self‐association in solution was observed by diffusion nuclear magnetic resonance spectroscopy. Copyright © 2007 John Wiley & Sons, Ltd. The synthesis and self‐association of chiral isotopically labeled trianglamine macrocycles under electrospray mass spectrometer conditions in an ion trap are described. Copyright © 2007 John Wiley & Sons, Ltd.