{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T06:32:36Z","timestamp":1775889156240,"version":"3.50.1"},"reference-count":0,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2024,6,25]],"date-time":"2024-06-25T00:00:00Z","timestamp":1719273600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Universidad Nacional de Quilmes","award":["11220200101081CO"],"award-info":[{"award-number":["11220200101081CO"]}]},{"name":"Universidad Nacional de Quilmes","award":["PICT2012 0811"],"award-info":[{"award-number":["PICT2012 0811"]}]},{"name":"Universidad Nacional de Quilmes","award":["2021-I-A-00984"],"award-info":[{"award-number":["2021-I-A-00984"]}]},{"name":"Secretar\u00eda de Ciencia y T\u00e9cnica de la Naci\u00f3n","award":["11220200101081CO"],"award-info":[{"award-number":["11220200101081CO"]}]},{"name":"Secretar\u00eda de Ciencia y T\u00e9cnica de la Naci\u00f3n","award":["PICT2012 0811"],"award-info":[{"award-number":["PICT2012 0811"]}]},{"name":"Secretar\u00eda de Ciencia y T\u00e9cnica de la Naci\u00f3n","award":["2021-I-A-00984"],"award-info":[{"award-number":["2021-I-A-00984"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Dihydroxyacetone phosphate (DHAP)-dependent aldolases catalyze the aldol addition of DHAP to a variety of aldehydes and generate compounds with two stereocenters. This reaction is useful to synthesize chiral acyclic nucleosides, which constitute a well-known class of antiviral drugs currently used. In such compounds, the chirality of the aliphatic chain, which mimics the open pentose residue, is crucial for activity. In this work, three DHAP-dependent aldolases: fructose-1,6-biphosphate aldolase from rabbit muscle, rhanmulose-1-phosphate aldolase from Thermotoga maritima, and fuculose-1-phosphate aldolase from Escherichia coli, were used as biocatalysts. Aldehyde derivatives of thymine and cytosine were used as acceptor substrates, generating new acyclic nucleoside analogues containing two new stereocenters with conversion yields between 70% and 90%. Moreover, structural analyses by molecular docking were carried out to gain insights into the diasteromeric excess observed.<\/jats:p>","DOI":"10.3390\/biom14070750","type":"journal-article","created":{"date-parts":[[2024,6,27]],"date-time":"2024-06-27T05:11:39Z","timestamp":1719465099000},"page":"750","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis of Chiral Acyclic Pyrimidine Nucleoside Analogues from DHAP-Dependent Aldolases"],"prefix":"10.3390","volume":"14","author":[{"given":"Mariano","family":"Nigro","sequence":"first","affiliation":[{"name":"Laboratorio de Biotransformaciones y Qu\u00edmica de \u00c1cidos Nucleicos, Universidad Nacional de Quilmes, Bernal 1876, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isra\u00e9l","family":"S\u00e1nchez-Moreno","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Bio-Org\u00e1nica, Instituto de Qu\u00edmica Org\u00e1nica General, Consejo Superior de Investigaciones Cient\u00edficas, 28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5651-8779","authenticated-orcid":false,"given":"Ra\u00fal","family":"Benito-Arenas","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Bio-Org\u00e1nica, Instituto de Qu\u00edmica Org\u00e1nica General, Consejo Superior de Investigaciones Cient\u00edficas, 28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ana L.","family":"Valino","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotransformaciones y Qu\u00edmica de \u00c1cidos Nucleicos, Universidad Nacional de Quilmes, Bernal 1876, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Adolfo M.","family":"Iribarren","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotransformaciones y Qu\u00edmica de \u00c1cidos Nucleicos, Universidad Nacional de Quilmes, Bernal 1876, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8552-058X","authenticated-orcid":false,"given":"Nicol\u00e1s","family":"Veiga","sequence":"additional","affiliation":[{"name":"Qu\u00edmica Inorg\u00e1nica, Departamento Estrella Campos, Facultad de Qu\u00edmica, Universidad de la Rep\u00fablica (UdelaR), Av. Gral. Flores 2124, Montevideo 11800, Uruguay"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2344-8743","authenticated-orcid":false,"given":"Eduardo","family":"Garc\u00eda-Junceda","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Bio-Org\u00e1nica, Instituto de Qu\u00edmica Org\u00e1nica General, Consejo Superior de Investigaciones Cient\u00edficas, 28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5563-6271","authenticated-orcid":false,"given":"Elizabeth S.","family":"Lewkowicz","sequence":"additional","affiliation":[{"name":"Laboratorio de Biotransformaciones y Qu\u00edmica de \u00c1cidos Nucleicos, Universidad Nacional de Quilmes, Bernal 1876, Argentina"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,25]]},"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/14\/7\/750\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:03:56Z","timestamp":1760108636000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/14\/7\/750"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,25]]},"references-count":0,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2024,7]]}},"alternative-id":["biom14070750"],"URL":"https:\/\/doi.org\/10.3390\/biom14070750","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,25]]}}}