Synthesis, self-association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer
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 investigati...
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| Published in | Journal of labelled compounds & radiopharmaceuticals Vol. 50; no. 13; pp. 1215 - 1223 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Chichester, UK
John Wiley & Sons, Ltd
01.11.2007
Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0362-4803 1099-1344 |
| DOI | 10.1002/jlcr.1449 |
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| Abstract | 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. |
|---|---|
| AbstractList | 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. 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 (C) 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. 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. |
| Author | Kuhnert, Nikolai Le-Gresley, Adam Nicolau, Daniel C. Lopez-Periago, Ana |
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| CitedBy_id | crossref_primary_10_1016_j_tetlet_2018_08_059 crossref_primary_10_1002_jms_1304 crossref_primary_10_1039_c004873a |
| Cites_doi | 10.1002/jlcr.1036 10.1002/hlca.19980810102 10.1002/anie.200300637 10.1021/ja00449a054 10.1021/ja064617d 10.1021/ac010284l 10.1016/j.tetlet.2005.08.155 10.1021/jo000623v 10.1038/19053 10.1039/b417941b 10.1002/jlcr.860 10.1039/b414747m 10.1039/cs9962500255 10.1016/S0957-4166(02)00065-4 10.1021/jo00086a062 10.1039/b212102f 10.1016/S0040-4039(02)00523-3 10.1039/a805809a 10.1039/b502378e 10.1063/1.1681876 10.1016/j.tetlet.2005.02.139 10.1016/j.tetlet.2006.02.100 10.1016/0021-9673(94)80417-6 10.1055/s-2005-922784 |
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| Issue | 13 |
| Keywords | 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 |
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| Notes | ArticleID:JLCR1449 istex:58BC16406B73D93E817E798C0ECE4E6E32C6701B Dedicated to the memory of Professor John Jones. ark:/67375/WNG-3N4MZ0XN-D |
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| PublicationTitle | Journal of labelled compounds & radiopharmaceuticals |
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| References | Kuhnert N, Rossignolo GM. Org Biomol Chem 2005; 3: 524-537. Gawronski J, Kolbon H, Kwit M, Katrusiak A. J Org Chem 2000; 65: 5768-5773. Coumbarides GS, Dingjan M, Eames J, Flinn A, Mptevalli M, Northern J, Yohannes Y. Tetrahedron Lett 2005; 46: 2897-2902. Prins LJ, Huskens J, Jong F de, Timmerman P, Reinhoudt DN. Nature 1999; 398: 498-502. Rebek Jr J. Chem Soc Rev 1996; 255-264. Suarez M, Branda N, Lehn JM. Helv Chim Acta 1998; 81: 1-13. Kuhnert N, Patel C, Jami F. Tetrahedron Lett 2005; 46: 7575-7579. Cole RB (ed.). ESI Mass Spectrometry: Fundamentals, Application and Instrumentation (1st edn). Wiley: Chichester, New York, Weinheim, Brisbane, Singapore, Toronto, 1999. Fales HM, Wright GJ. J Am Chem Soc 1977; 99: 2339-2340. Schneider HJ, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley: Chichester, New York, Weinheim, Brisbane, Singapore, Toronto, 2000. Kuhnert N, Tang B. Tetrahedron Lett 2006; 47: 2985-2988. Chen Y, Avrat L, Frish L. Angew Chem Int Ed Engl 2005; 44: 520-554. Searcy JQ, Fenn JB. J Chem Phys 1974; 61: 5282-5288. Coumbarides GS, Dingjan M, Eames J, Flinn A, Mptevalli M, Northern J, Yohannes Y. Synlett 2006; 101-105. Winkler JF, Medina R, Winkler J, Krause H. J Chromatogr A 1994; 666: 549-556. Larrow JF, Jacobsen EN. J Org Chem 1994; 59: 1939-1941. Kuhnert N, Le-Gresley A. Org Biomol Chem 2005; 3: 2175-2182. Yang P, Xu R, Nanita SC, Cooks RC. J Am Chem Soc 2006; 128: 17074-17086. Kuhnert N, Strassnig C, Lopez-Periago A. Tetrahedron Asym 2002; 13: 123-128. Kuhnert N, Lopez-Periago A, Rossignolo GM. Org Biomol Chem 2003; 1: 1157-1170. Cooks RG, Zhang D, Koch KJ, Gozzo FC, Eberlin MN. Anal Chem 2001; 73: 3646-3655. Eames J, Suggate MJ. J Labell Compd Radiopharm 2004; 47: 705-717. Kuhnert N, Lopeez-Periago A. Tetrahedron Lett 2002; 43: 3329-3332. Kuhnert N, Patel C, Burzlaff N, Lopez-Periago A. Org Biomol Chem 2005; 3: 1911-1921. Coumbarides GS, Dingjan J, Eames J, Suggate JM. J Label Compd Radiopharm 2006; 49: 153-161. Ishow E, Gourdon A, Launay JP. Chem Commun 1998; 1909-1910. 1994; 666 2000 1974; 61 2004; 47 2000; 65 2006; 49 2002; 13 2002; 43 2006; 47 1998 1996 2006 1998; 81 1977; 99 1994; 59 2005; 3 1999; 398 2003; 1 2006; 128 2001; 73 2005; 44 2005; 46 1999 Schneider HJ (e_1_2_1_2_2) 2000 Coumbarides GS (e_1_2_1_19_2) 2006 e_1_2_1_23_2 e_1_2_1_20_2 e_1_2_1_21_2 e_1_2_1_26_2 e_1_2_1_27_2 e_1_2_1_24_2 e_1_2_1_25_2 Cole RB (e_1_2_1_22_2) 1999 e_1_2_1_6_2 e_1_2_1_7_2 e_1_2_1_4_2 e_1_2_1_5_2 e_1_2_1_11_2 e_1_2_1_3_2 e_1_2_1_12_2 e_1_2_1_10_2 e_1_2_1_15_2 e_1_2_1_16_2 e_1_2_1_13_2 e_1_2_1_14_2 e_1_2_1_8_2 e_1_2_1_17_2 e_1_2_1_9_2 e_1_2_1_18_2 Cooks, RG (WOS:000170274400026) 2001; 73 Kuhnert, N (WOS:000236651500031) 2006; 47 Kuhnert, N (WOS:000232572200024) 2005; 46 Coumbarides, GS (WOS:000235976900008) 2006; 49 Eames, J (WOS:000224594000009) 2004; 47 Ishow, E (WOS:000075737000063) 1998 Kuhnert, N (WOS:000175421200018) 2002; 43 Rebek, J (WOS:A1996VT22500004) 1996; 25 SEARCY, JQ (WOS:A1974V247000044) 1974; 61 Prins, LJ (WOS:000079662800044) 1999; 398 SCHNEIDER HJ (WOS:000253063800013.22) 2000 Kuhnert, N (WOS:000229067300015) 2005; 3 LARROW, JF (WOS:A1994NF80700062) 1994; 59 Kuhnert, N (WOS:000181919400015) 2003; 1 Kuhnert, N (WOS:000226593700023) 2005; 3 Cohen, Y (WOS:000226537300004) 2005; 44 Yang, PX (WOS:000242941600115) 2006; 128 Coumbarides, GS (WOS:000228195200038) 2005; 46 Gawronski, J (WOS:000089310200042) 2000; 65 Coumbarides, GS (WOS:000234469600019) 2006 WINKLER, FJ (WOS:A1994NK23000052) 1994; 666 FALES, HM (WOS:A1977CZ99900054) 1977; 99 Kuhnert, N (WOS:000175109200005) 2002; 13 COLE RB (WOS:000253063800013.2) 1999 Suarez, M (WOS:000071737400001) 1998; 81 Kuhnert, N (WOS:000229373500022) 2005; 3 |
| References_xml | – reference: Rebek Jr J. Chem Soc Rev 1996; 255-264. – reference: Kuhnert N, Tang B. Tetrahedron Lett 2006; 47: 2985-2988. – reference: Kuhnert N, Lopez-Periago A, Rossignolo GM. Org Biomol Chem 2003; 1: 1157-1170. – reference: Cole RB (ed.). ESI Mass Spectrometry: Fundamentals, Application and Instrumentation (1st edn). Wiley: Chichester, New York, Weinheim, Brisbane, Singapore, Toronto, 1999. – reference: Ishow E, Gourdon A, Launay JP. Chem Commun 1998; 1909-1910. – reference: Searcy JQ, Fenn JB. J Chem Phys 1974; 61: 5282-5288. – reference: Kuhnert N, Lopeez-Periago A. Tetrahedron Lett 2002; 43: 3329-3332. – reference: Eames J, Suggate MJ. J Labell Compd Radiopharm 2004; 47: 705-717. – reference: Suarez M, Branda N, Lehn JM. Helv Chim Acta 1998; 81: 1-13. – reference: Coumbarides GS, Dingjan J, Eames J, Suggate JM. J Label Compd Radiopharm 2006; 49: 153-161. – reference: Schneider HJ, Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (1st edn). Wiley: Chichester, New York, Weinheim, Brisbane, Singapore, Toronto, 2000. – reference: Winkler JF, Medina R, Winkler J, Krause H. J Chromatogr A 1994; 666: 549-556. – reference: Chen Y, Avrat L, Frish L. Angew Chem Int Ed Engl 2005; 44: 520-554. – reference: Cooks RG, Zhang D, Koch KJ, Gozzo FC, Eberlin MN. Anal Chem 2001; 73: 3646-3655. – reference: Coumbarides GS, Dingjan M, Eames J, Flinn A, Mptevalli M, Northern J, Yohannes Y. Tetrahedron Lett 2005; 46: 2897-2902. – reference: Kuhnert N, Patel C, Jami F. Tetrahedron Lett 2005; 46: 7575-7579. – reference: Gawronski J, Kolbon H, Kwit M, Katrusiak A. J Org Chem 2000; 65: 5768-5773. – reference: Fales HM, Wright GJ. J Am Chem Soc 1977; 99: 2339-2340. – reference: Kuhnert N, Rossignolo GM. Org Biomol Chem 2005; 3: 524-537. – reference: Yang P, Xu R, Nanita SC, Cooks RC. J Am Chem Soc 2006; 128: 17074-17086. – reference: Coumbarides GS, Dingjan M, Eames J, Flinn A, Mptevalli M, Northern J, Yohannes Y. 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| Snippet | The synthesis and self‐association of chiral isotopically labeled trianglamine macrocycles under electrospray mass spectrometer conditions in an ion trap are... The synthesis and self-association of chiral isotopically labeled trianglamine macrocycles under electrospray mass spectrometer conditions in an ion trap are... |
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| SubjectTerms | 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 |
| Title | Synthesis, self-association and chiroselectivity of isotopically labeled trianglamine macrocycles in the ion trap mass spectrometer |
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