000145723 001__ 145723
000145723 005__ 20250923084435.0
000145723 0247_ $$2doi$$a10.1021/acsomega.4c07412
000145723 0248_ $$2sideral$$a140640
000145723 037__ $$aART-2024-140640
000145723 041__ $$aeng
000145723 100__ $$aBretón, Carmen
000145723 245__ $$aExploring Photoredox Catalytic Reactions as an Entry to Glycosyl-a-amino Acids
000145723 260__ $$c2024
000145723 5060_ $$aAccess copy available to the general public$$fUnrestricted
000145723 5203_ $$aThe synthesis of glycosyl-α-amino acids presents a significant challenge due to the need for precise glycosidic linkages connecting carbohydrate moieties to amino acids while maintaining stereo- and regiochemical fidelity. Classical methods relying on ionic intermediates (2e–) often involve intricate synthetic procedures, particularly when dealing with 2-N-acetamido-2-deoxyglycosides linked to α-amino acids─a crucial class of glycoconjugates that play important biological roles. Considering the growing prominence of photocatalysis, this study explores various photoredox catalytic approaches to achieving glycosylation reactions. Our focus lies on the notoriously difficult case of 2-N-acetamido-2-deoxyglycosyl-α-amino acids, which could be obtained efficiently by two methodologies that involved, on the one hand, photoredox Giese reactions using a chiral dehydroalanine (Dha) as an electron density-deficient alkene in these radical 1,4-additions and, on the other hand, photoredox glycosylations using selenoglycosides as glycosyl donors and hydroxyl groups of protected amino acids as acceptors.
000145723 536__ $$9info:eu-repo/grantAgreement/EC/H2020/956544/EU/Directing the immune response through designed nanomaterials/DIRNANO$$9This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement No H2020 956544-DIRNANO$$9info:eu-repo/grantAgreement/ES/MICINN/PDC2022-133725-C21$$9info:eu-repo/grantAgreement/ES/MICINN/PID2021-127622OB-I00
000145723 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000145723 590__ $$a4.3$$b2024
000145723 592__ $$a0.773$$b2024
000145723 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b81 / 239 = 0.339$$c2024$$dQ2$$eT2
000145723 593__ $$aChemical Engineering (miscellaneous)$$c2024$$dQ1
000145723 593__ $$aChemistry (miscellaneous)$$c2024$$dQ2
000145723 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000145723 700__ $$aOroz, Paula
000145723 700__ $$aTorres, Miguel
000145723 700__ $$aZurbano, María M.
000145723 700__ $$0(orcid)0000-0002-7063-1292$$aGarcía-Orduña, Pilar
000145723 700__ $$aAvenoza, Alberto
000145723 700__ $$aBusto, Jesús H.
000145723 700__ $$aCorzana, Francisco
000145723 700__ $$aPeregrina, Jesús M.
000145723 773__ $$g9, 45 (2024), 45437-45446$$pACS Omega$$tACS OMEGA$$x2470-1343
000145723 8564_ $$s2970708$$uhttps://zaguan.unizar.es/record/145723/files/texto_completo.pdf$$yVersión publicada
000145723 8564_ $$s3237848$$uhttps://zaguan.unizar.es/record/145723/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000145723 909CO $$ooai:zaguan.unizar.es:145723$$particulos$$pdriver
000145723 951__ $$a2025-09-22-14:46:13
000145723 980__ $$aARTICLE