{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,27]],"date-time":"2026-02-27T17:46:49Z","timestamp":1772214409972,"version":"3.50.1"},"reference-count":27,"publisher":"Wiley","issue":"18","license":[{"start":{"date-parts":[[2014,8,5]],"date-time":"2014-08-05T00:00:00Z","timestamp":1407196800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"Chinese National Natural Science Foundation","doi-asserted-by":"crossref","award":["21305115, 21375113, and 21173178"],"award-info":[{"award-number":["21305115, 21375113, and 21173178"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2014,9,30]]},"abstract":"<jats:sec>\n                    <jats:title>RATIONALE<\/jats:title>\n                    <jats:p>\u03b1\u2010Amino phosphonates with intrinsic biological activities have been used in a wide variety of applications. Because of the widespread existence of natural organophosphorus compounds containing P\u2013C bonds such as the \u03b1\u2010amino phosphonates, it is important to investigate the gas\u2010phase chemistry of P\u2013C bonds in order to determine their basic properties, which might provide some insights into their biosynthesis and catalytic cleavage.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>METHODS<\/jats:title>\n                    <jats:p>Twenty \u03b1\u2010amino phosphonates were successfully synthesized and their fragmentation behavior was systematically investigated using in\u2010solution deuterium labeling in combination with high\u2010resolution Fourier transform ion cyclotron resonance (FTICR) electrospray ionization tandem mass spectrometry.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>The fragmentation pathways of twenty \u03b1\u2010amino phosphonates with different chemical structures were systematically studied. In general, P\u2013C bonds could be easily cleaved via a novel intramolecular hydrogen atom migration from the amino group to the phosphoryl group through a five\u2010membered\u2010ring intermediate in the gas phase. A possible mechanism of the rearrangement of \u03b1\u2010amino phosphonates is proposed.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSIONS<\/jats:title>\n                    <jats:p>An interesting intramolecular hydrogen atom migration between the amino and phosphoryl groups was observed with cleavage of the P\u2013C bond in the molecule through a five\u2010membered\u2010ring intermediate. This characteristic fragmentation pathway not only provides some insights into the basic chemistry of compounds with P\u2013C bonds, but could also have some applications in the structural determination of the \u03b1\u2010amino phosphonate analogues. Copyright \u00a9 2014 John Wiley &amp; Sons, Ltd.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.6984","type":"journal-article","created":{"date-parts":[[2014,8,5]],"date-time":"2014-08-05T06:19:58Z","timestamp":1407219598000},"page":"1964-1970","source":"Crossref","is-referenced-by-count":5,"title":["Cleavage of phosphorus\u2013carbon (P\u2013C) bonds of \u03b1\u2010amino phosphonates with intramolecular hydrogen migration in the gas phase using electrospray ionization tandem mass spectrometry"],"prefix":"10.1002","volume":"28","author":[{"given":"Yuzhen","family":"Gao","sequence":"first","affiliation":[{"name":"Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering Xiamen University  Xiamen 361005 P. R. 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