دورية أكاديمية
Intramolecular interactions and the neutral loss of ammonia from collisionally activated, protonated ω-aminoalkyl-3-hydroxyfurazans.
| العنوان: | Intramolecular interactions and the neutral loss of ammonia from collisionally activated, protonated ω-aminoalkyl-3-hydroxyfurazans. |
|---|---|
| المؤلفون: | Grossert JS; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada., Boschi D; Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, Torino, Italy., Lolli ML; Dipartimento di Scienza e Tecnologia del Farmaco (DSTF), Università degli Studi di Torino, Torino, Italy., White RL; Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada. |
| المصدر: | European journal of mass spectrometry (Chichester, England) [Eur J Mass Spectrom (Chichester)] 2024 Feb; Vol. 30 (1), pp. 38-46. Date of Electronic Publication: 2023 Nov 17. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: SAGE Publishing Country of Publication: England NLM ID: 101124748 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1751-6838 (Electronic) Linking ISSN: 14690667 NLM ISO Abbreviation: Eur J Mass Spectrom (Chichester) Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: | Publication: 2017- : London, U.K. : SAGE Publishing Original Publication: Chichester, West Sussex, U.K. : IM Publications, c2000- |
| مستخلص: | Gas phase fragmentation reactions of monoprotonated 4-(3-aminopropyl)- and 4-(4-aminobutyl)-3-hydroxyfurazan were investigated to examine potential interactions between functional groups. The two heterocyclic alkyl amines were ionized by electrospray ionization (ESI, positive mode) and fragmented using tandem mass spectrometry (MS/MS). The fragmentation pathways were characterized using pseudo MS 3 experiments, precursor-ion scans, and density functional computations. For both heterocyclic ions, loss of ammonia was the only fragmentation process observed at low collision energies. Computational analysis indicated that the most feasible mechanism was intramolecular nucleophilic displacement of ammonia from the protonated ω-aminoalkyl side chain by N5 of the furazan ring. The alkylated nitrogen in the resulting bicyclic product ion facilitated N-O bond cleavage; subsequent neutral losses of nitric oxide (NO) and carbon monoxide (CO) occurred by homolytic bond cleavages. Next in the multistep sequence, neutral loss of ethylene from a radical cation was observed. A less favorable, competing fragmentation pathway of protonated 4-(3-aminopropyl)-3-hydroxyfurazan was consistent with cleavage of the 3-hydroxyfurazan ring and losses of NO and CO. Overall, the similar fragmentation behavior found for protonated 4-(3-aminopropyl)- and 4-(4-aminobutyl)-3-hydroxyfurazan differed from that previously characterized for furazan analogs with shorter alkyl chains. These observations demonstrate that a small change in the structure of multifunctional, heterocyclic alkyl amines may significantly influence interactions between distinct functional groups and the nature of the fragmentation process. Competing Interests: Declaration of conflicting interestsThe author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article. |
| References: | J Mol Graph Model. 2004 Sep;23(1):51-8. (PMID: 15331053) Phys Chem Chem Phys. 2008 Nov 28;10(44):6615-20. (PMID: 18989472) Bioorg Med Chem. 2012 Oct 1;20(19):5678-98. (PMID: 22902032) Mass Spectrom Rev. 2011 May-Jun;30(3):479-90. (PMID: 21500245) Mass Spectrom Rev. 2004 Jan-Feb;23(1):1-24. (PMID: 14625889) J Pharm Biomed Anal. 1999 Jun;20(1-2):129-36. (PMID: 10704016) J Am Soc Mass Spectrom. 2019 Oct;30(10):2060-2067. (PMID: 31338738) Mass Spectrom Rev. 2007 May-Jun;26(3):340-69. (PMID: 17405144) Rapid Commun Mass Spectrom. 2015 Mar 30;29(6):515-20. (PMID: 26160417) J Mass Spectrom. 2004 Mar;39(3):295-302. (PMID: 15039937) ChemMedChem. 2013 Mar;8(3):385-95. (PMID: 23361977) Curr Med Chem. 2022;29(13):2203-2234. (PMID: 34420501) Bioorg Chem. 2020 Nov;104:104240. (PMID: 32906036) Eur J Med Chem. 2017 Mar 31;129:287-302. (PMID: 28235702) Eur J Med Chem. 2017 Oct 20;139:936-946. (PMID: 28881288) Eur J Med Chem. 2012 Mar;49:102-9. (PMID: 22245049) J Mass Spectrom. 1996 Aug;31(8):879-84. (PMID: 8799314) Molecules. 2019 Oct 25;24(21):. (PMID: 31731387) Rapid Commun Mass Spectrom. 2012 Nov 15;26(21):2509-16. (PMID: 23008068) Rapid Commun Mass Spectrom. 2014 May 15;28(9):1045-50. (PMID: 24677526) ACS Med Chem Lett. 2019 Jan 28;10(4):437-443. (PMID: 30996776) J Mass Spectrom. 2017 Sep;52(9):591-596. (PMID: 28677141) J Mass Spectrom. 2012 Aug;47(8):1059-64. (PMID: 22899515) J Agric Food Chem. 2023 Nov 29;71(47):18087-18122. (PMID: 36961953) Rapid Commun Mass Spectrom. 2018 Aug 30;32(16):1403-1413. (PMID: 29756659) J Med Chem. 2010 May 27;53(10):4110-8. (PMID: 20408529) Mass Spectrom Rev. 2011 Jul-Aug;30(4):626-63. (PMID: 21294151) Talanta. 2014 Jul;125:242-7. (PMID: 24840440) J Med Chem. 2006 Jul 13;49(14):4442-6. (PMID: 16821803) Mass Spectrom Rev. 2012 Nov-Dec;31(6):626-65. (PMID: 22829116) J Mass Spectrom. 2021 Jul;56(7):e4770. (PMID: 34120394) Rapid Commun Mass Spectrom. 2006;20(11):1715-23. (PMID: 16676312) J Mass Spectrom. 2015 Dec;50(12):1433-7. (PMID: 26634978) J Am Soc Mass Spectrom. 2023 Apr 5;34(4):710-719. (PMID: 36951239) J Mass Spectrom. 2010 Feb;45(2):146-56. (PMID: 19911413) J Med Chem. 2011 Apr 28;54(8):2529-91. (PMID: 21413808) |
| فهرسة مساهمة: | Keywords: 3-hydroxyfurazan; Collisional activation; DFT computations; ESI(+)-MS/MS; fragmentation mechanisms; heterocycles |
| تواريخ الأحداث: | Date Created: 20231117 Latest Revision: 20240127 |
| رمز التحديث: | 20240127 |
| مُعرف محوري في PubMed: | PMC10809737 |
| DOI: | 10.1177/14690667231214672 |
| PMID: | 37974410 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1751-6838 |
|---|---|
| DOI: | 10.1177/14690667231214672 |