{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:24:07Z","timestamp":1760549047804,"version":"build-2065373602"},"reference-count":25,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2010,10,28]],"date-time":"2010-10-28T00:00:00Z","timestamp":1288224000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2010,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Two routes for the synthesis of <jats:italic>N<\/jats:italic>\u2010ethyl\u2010<jats:italic>N<\/jats:italic>\u2010(4\u2010nitrophenylsulfonyl)\u2010\u03b1,\u03b2\u2010dehydroamino acid derivatives from serine, threonine and phenylserine derivatives are presented. One route consists of dehydration of <jats:italic>N<\/jats:italic>\u2010(4\u2010nitrophenylsulfonyl)\u2010\u03b2\u2010hydroxyamino acid esters with di\u2010<jats:italic>tert<\/jats:italic>\u2010butyl dicarbonate catalyzed by 4\u2010(dimethylamino)pyridine, followed by alkylation of the <jats:italic>N<\/jats:italic>\u2010(4\u2010nitrophenylsulfonyl)\u2010\u03b1,\u03b2\u2010dehydroamino acid methyl esters obtained with triethyloxonium tetrafluoroborate. The second strategy applied the same procedures but in inverse order: alkylation followed by dehydration. These methods made it possible to obtain for the first time, new non\u2010natural amino acids, which incorporate both an <jats:italic>N<\/jats:italic>\u2010ethyl and an \u03b1,\u03b2\u2010dehydro moiety.<\/jats:p>","DOI":"10.1002\/ejoc.201001302","type":"journal-article","created":{"date-parts":[[2010,10,28]],"date-time":"2010-10-28T19:38:58Z","timestamp":1288294738000},"page":"6731-6735","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Synthesis of Novel Nonproteinogenic Amino Acids: <i>N<\/i>\u2010Ethyl\u2010\u03b1,\u03b2\u2010dehydroamino Acid Methyl Esters"],"prefix":"10.1002","volume":"2010","author":[{"given":"Lu\u00eds S.","family":"Monteiro","sequence":"first","affiliation":[]},{"given":"Joanna","family":"Ko\u0142oma\u0144ska","sequence":"additional","affiliation":[]},{"given":"Ana C.","family":"Suarez","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2010,10,28]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1055\/b-003-111718"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030024z"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198500773"},{"volume-title":"Peptides: Proceedings of the 7th American Peptide Symposium","year":"1981","author":"Shuman R. T.","key":"e_1_2_6_4_2"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1387(199901)5:1<56::AID-PSC186>3.0.CO;2-J"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.3891\/acta.chem.scand.48-0324"},{"volume-title":"Peptides 1996: Proceedings of the 24th European Peptide Symposium","year":"1998","author":"Athanassopoulos C.","key":"e_1_2_6_7_2"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/1097-0282(2000)55:2<123::AID-BIP30>3.0.CO;2-F"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-008-0221-8"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000256"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00040a024"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199110513"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030105v"},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-7091-8545-2_3"},{"volume-title":"The Peptides","year":"1983","author":"Noda K.","key":"e_1_2_6_18_2"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1988-27503"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)85989-X"},{"key":"e_1_2_6_21_2","unstructured":"R. H. Mazur D. R. Pilipauskas W. de Gruyter) 1983 Peptides 1982 Berlin"},{"key":"e_1_2_6_22_2","first-page":"1","volume":"1","author":"Bonauer C.","year":"2006","journal-title":"Synthesis"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/a904730a"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700669"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300103"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201001302","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201001302","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T15:59:29Z","timestamp":1760543969000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201001302"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,10,28]]},"references-count":25,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2010,12]]}},"alternative-id":["10.1002\/ejoc.201001302"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201001302","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"type":"print","value":"1434-193X"},{"type":"electronic","value":"1099-0690"}],"subject":[],"published":{"date-parts":[[2010,10,28]]},"assertion":[{"value":"2010-09-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2010-10-28","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}