{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,29]],"date-time":"2025-10-29T03:50:19Z","timestamp":1761709819977,"version":"build-2065373602"},"reference-count":33,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,5]],"date-time":"2021-02-05T00:00:00Z","timestamp":1612483200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100014440","name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades","doi-asserted-by":"publisher","award":["RTI2018-096182-B-I00"],"award-info":[{"award-number":["RTI2018-096182-B-I00"]}],"id":[{"id":"10.13039\/100014440","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002943","name":"Departament d'Innovaci\u00f3, Universitats i Empresa, Generalitat de Catalunya","doi-asserted-by":"publisher","award":["2017 SGR 208"],"award-info":[{"award-number":["2017 SGR 208"]}],"id":[{"id":"10.13039\/501100002943","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The binding and stabilizing effect of arginine residues in certain aldolases served as inspiring source for the development of a family of amino acylguanidine organocatalysts. Screening and optimization led to identify the threonine derivative as the most suitable catalyst for the asymmetric aldol addition of hydroxyacetone, affording the syn diastereomer in high ee. In contrast, the proline derivative yielded the anti diasteromer. MMFF models suggest the presence of an extensive hydrogen bonding network between the acylguanidinium group and the reaction intermediates.<\/jats:p>","DOI":"10.3390\/molecules26040826","type":"journal-article","created":{"date-parts":[[2021,2,5]],"date-time":"2021-02-05T08:33:48Z","timestamp":1612514028000},"page":"826","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Amino Acylguanidines as Bioinspired Catalysts for the Asymmetric Aldol Reaction"],"prefix":"10.3390","volume":"26","author":[{"given":"Ciril","family":"Jimeno","sequence":"first","affiliation":[{"name":"Department of Biological Chemistry, Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, E08034 Barcelona, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"8130","DOI":"10.1021\/acscatal.7b03398","article-title":"Catalytic roles of histidine and arginine in pyruvate class II aldolase: A perspective from QM\/MM metadynamics","volume":"7","author":"Huang","year":"2017","journal-title":"ACS Catal."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/j.abb.2008.01.005","article-title":"Directed evolution of aldolases for exploitation in synthetic organic chemistry","volume":"474","author":"Bolt","year":"2008","journal-title":"Arch. 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