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A novel methyl group migration in the gas phase was observed in ESI-MS\n                    <jats:sup>2<\/jats:sup>\n                    of the sodium adducts of amino acid methyl ester of phosphorodiamidates of 2\u2032,3\u2032-didehydro-2\u2032,3\u2032-dideox y thymidine (d4T). The proposed structures of the rearrangement ions were confirmed by high-resolution tandem mass spectrometry. A possible mechanism involving the pentacoordinate phosphoric\u2013carboxylic phosphate anhydride was proposed, in which a seven-membered ring intermediate was formed by coordination with the metal ion between the phosphoryl group and carbonyl oxygen atom. Thus, the intrinsic properties of phosphoryl group might be the key factors responsible for this migration.\n                  <\/jats:p>","DOI":"10.1255\/ejms.1111","type":"journal-article","created":{"date-parts":[[2011,7,1]],"date-time":"2011-07-01T05:47:00Z","timestamp":1309499220000},"page":"187-195","update-policy":"https:\/\/doi.org\/10.1177\/sage-journals-update-policy","source":"Crossref","is-referenced-by-count":1,"title":["Identification of Amino Acid Phosphorodiamidates of Antiviral Nucleosides Using Electrospray Ionisation Tandem Mass Spectrometry"],"prefix":"10.1177","volume":"17","author":[{"given":"Juntao","family":"Cui","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, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiang","family":"Gao","sequence":"additional","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, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aiting","family":"Fan","sequence":"additional","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, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shuangyan","family":"Zhang","sequence":"additional","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, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yan","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemical Biology and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pengxiang","family":"Xu","sequence":"additional","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, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yufen","family":"Zhao","sequence":"additional","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, PR China"},{"name":"The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, School of Sciences, Tsinghua University, Beijing 100084, PR China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"179","published-online":{"date-parts":[[2011,4,1]]},"reference":[{"key":"bibr1-ejms.1111","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-199652060-00014"},{"key":"bibr2-ejms.1111","doi-asserted-by":"publisher","DOI":"10.1016\/0166-3542(95)00016-F"},{"key":"bibr3-ejms.1111","doi-asserted-by":"publisher","DOI":"10.1358\/dof.1993.018.04.203101"},{"key":"bibr4-ejms.1111","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1016\/S0026-895X(25)11067-5","volume":"39","author":"Chen C.","year":"1991","journal-title":"Mol. 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