{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T17:39:56Z","timestamp":1791221996618,"version":"4.1.0"},"reference-count":43,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/100007594","name":"Univerzita Komensk\u00e9ho v Bratislave","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007594","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003193","name":"Ministerstvo \u0161kolstva vedy v\u00fdskumu a \u0161portu Slovenskej republiky","doi-asserted-by":"publisher","award":["09I03-03-V04-00751"],"award-info":[{"award-number":["09I03-03-V04-00751"]}],"id":[{"id":"10.13039\/501100003193","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003193","name":"Ministerstvo \u0161kolstva vedy v\u00fdskumu a \u0161portu Slovenskej republiky","doi-asserted-by":"publisher","award":["09I03-03-V05-00008"],"award-info":[{"award-number":["09I03-03-V05-00008"]}],"id":[{"id":"10.13039\/501100003193","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Carbohydrate Research"],"published-print":{"date-parts":[[2026,1]]},"DOI":"10.1016\/j.carres.2025.109742","type":"journal-article","created":{"date-parts":[[2025,11,16]],"date-time":"2025-11-16T07:04:13Z","timestamp":1763276653000},"page":"109742","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":1,"special_numbering":"C","title":["A \u2018chiron\u2019 approach to divergent synthesis of 2-C-tridecyl 1-N-iminosugar mimetics and their anticancer profile"],"prefix":"10.1016","volume":"559","author":[{"given":"Monika","family":"Tvrdo\u0148ov\u00e1","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Michal\u010din","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tatiana","family":"Pon\u010d\u00e1kov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuliia","family":"Zuzak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martina Bago","family":"Pil\u00e1tov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juraj","family":"Kuch\u00e1r","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miroslava","family":"Liteck\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9359-2276","authenticated-orcid":false,"given":"Miroslava","family":"Martinkov\u00e1","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.carres.2025.109742_bib1a","doi-asserted-by":"crossref","first-page":"1645","DOI":"10.1016\/S0957-4166(00)00113-0","article-title":"Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application","volume":"11","author":"Asano","year":"2000","journal-title":"Tetrahedron Asymmetry"},{"key":"10.1016\/j.carres.2025.109742_bib1b","doi-asserted-by":"crossref","first-page":"645","DOI":"10.1016\/j.tetasy.2009.02.048","article-title":"Iminosugars: from botanical curiosities to licensed drugs","volume":"20","author":"Winchester","year":"2009","journal-title":"Tetrahedron Asymmetry"},{"key":"10.1016\/j.carres.2025.109742_bib1c","doi-asserted-by":"crossref","first-page":"652","DOI":"10.1016\/j.tetasy.2009.03.013","article-title":"A silver-lined anniversary of Fleet Iminosugars: 1984\u20122009, from DIM to DRAM to LABNAc","volume":"20","author":"Davis","year":"2009","journal-title":"Tetrahedron Asymmetry"},{"key":"10.1016\/j.carres.2025.109742_bib1d","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1055\/s-0033-1340822","article-title":"Searching for Glycomimetics That Target Protein Misfolding in Rare Diseases: Successes, Failures, and Unexpected Progress Made in Organic Synthesis","volume":"25","author":"Compain","year":"2014","journal-title":"Synlett"},{"key":"10.1016\/j.carres.2025.109742_bib1e","doi-asserted-by":"crossref","first-page":"6812","DOI":"10.1002\/ejoc.201800943","article-title":"Synthetic Pathways to 3,4,5-trihydroxypiperidines from the Chiral Pool","volume":"2018","author":"Wood","year":"2018","journal-title":"Eur. J. Org. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib1f","doi-asserted-by":"crossref","first-page":"5439","DOI":"10.1039\/D1OB00382H","article-title":"Iminosugars as glycosyltransferase inhibitors","volume":"19","author":"Conforti","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib1g","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2022.115056","article-title":"Nanomolar \u03b2-glucosidase and \u03b2-galactosidase inhibition by enantiomeric \u03b1-1-C-alkyl-1,4-dideoxy-1,4-iminoarabinitol derivatives","volume":"247","author":"Zi","year":"2023","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib2a","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1021\/cr000433k","article-title":"Recent Developments of Transition-State Analogue Glycosidase Inhibitors of Non-Natural Product Origin","volume":"102","author":"Lillelund","year":"2002","journal-title":"Chem. Rev."},{"key":"10.1016\/j.carres.2025.109742_bib2b","doi-asserted-by":"crossref","first-page":"8848","DOI":"10.1002\/anie.200902620","article-title":"Glycosphingolipids\u2012Nature, Function, and Pharmacological Modulation","volume":"48","author":"Wennekes","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1016\/j.carres.2025.109742_bib2c","doi-asserted-by":"crossref","first-page":"1139","DOI":"10.2174\/1389557511009011139","article-title":"Recent Advances in the Allosteric Inhibition of Glycogen Phosphorylase","volume":"10","author":"Loughlin","year":"2010","journal-title":"Mini Rev. Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib2d","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/B978-0-12-385518-3.00004-3","article-title":"Chapter 4 - Imino sugars and glycosyl hydrolases: Historical Context, current aspects, emerging trends","volume":"66","author":"St\u00fctz","year":"2011","journal-title":"Adv. Carbohydr. Chem. Biochem."},{"key":"10.1016\/j.carres.2025.109742_bib2e","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1039\/C5OB02223A","article-title":"Docking study and biological evaluation of pyrrolidine-based iminosugars as pharmacological chaperones for Gaucher disease","volume":"14","author":"Kato","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib2f","doi-asserted-by":"crossref","first-page":"7852","DOI":"10.1039\/D0OB01522A","article-title":"Concise asymmetric synthesis of new enantiomeric C-alkyl pyrrolidines acting as pharmacological chaperones against Gaucher disease","volume":"18","author":"Castellan","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib2g","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2021.113716","article-title":"Synthesis and glycosidase inhibition of 5-C-alkyl-DNJ and 5-C-alkyl-l-ido-DNJ derivatives","volume":"224","author":"Lu","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib2h","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2022.114230","article-title":"Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives","volume":"233","author":"Wang","year":"2022","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib3","first-page":"66","article-title":"Nojirimycin, a new antibiotic. II. Isolation, characterization and biological activity","volume":"20","author":"Ishida","year":"1967","journal-title":"J. Antibiot."},{"key":"10.1016\/j.carres.2025.109742_bib4","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/S0301-4770(08)60404-2","article-title":"Chapter 13 alkaloidal glycosidase inhibitors from plants","volume":"43","author":"Fellows","year":"1989","journal-title":"J. Chromatogr. Libr."},{"key":"10.1016\/j.carres.2025.109742_bib5","unstructured":"According to the IUPAC Nomenclature of Carbohydrates, Recommendations 1996 (the rules 2-Carb-34.1 and 2-Carb-34.2) the azasugars (e.g. 1.5-dideoxy-1,5-iminoxylitol) are defined as compounds, in Which a Nitrogen Atom Replaces the Anomeric Carbon of Monosaccharides, and a Carbon Atom Replaces the Endocyclic Oxygen."},{"key":"10.1016\/j.carres.2025.109742_bib6","doi-asserted-by":"crossref","first-page":"977","DOI":"10.1039\/c39790000977","article-title":"Isolation and structure of an unusual cyclic amino alditol from a legume","volume":"1979","author":"Fellows","year":"1979","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"10.1016\/j.carres.2025.109742_bib7","doi-asserted-by":"crossref","first-page":"628","DOI":"10.2174\/0929867327666200114112728","article-title":"1-Deoxynojirimycin and its derivatives: a mini review of the literature","volume":"28","author":"Wang","year":"2021","journal-title":"Curr. Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib8","doi-asserted-by":"crossref","first-page":"41287","DOI":"10.1074\/jbc.M006927200","article-title":"Structural basis for catalysis and inhibition of N-Glycan processing class I \u03b11,2-Mannosidases","volume":"275","author":"Vallee","year":"2000","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib9","first-page":"332","article-title":"Three trihydroxypiperidines, glycosidase inhibitors, from Eupatorium fortunei turz","volume":"49","author":"Sekioka","year":"1995","journal-title":"Nat. Med."},{"key":"10.1016\/j.carres.2025.109742_bib10","doi-asserted-by":"crossref","first-page":"1356","DOI":"10.1002\/cbic.200600217","article-title":"Design and synthesis of highly potent and selective pharmacological chaperones for the treatment of Gaucher\ua78cs disease","volume":"7","author":"Compain","year":"2006","journal-title":"Chembiochem"},{"key":"10.1016\/j.carres.2025.109742_bib11","doi-asserted-by":"crossref","first-page":"3321","DOI":"10.1039\/b307455b","article-title":"A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies","volume":"1","author":"Pandey","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib12a","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1111\/cbdd.13182","article-title":"Biological activities of 3,4,5-trihydroxypiperidines and their N- and O-derivatives","volume":"92","author":"Prichard","year":"2018","journal-title":"Chem. Biol. Drug Des."},{"key":"10.1016\/j.carres.2025.109742_bib12b","doi-asserted-by":"crossref","first-page":"3383","DOI":"10.1021\/acs.joc.3c02817","article-title":"Lewis Acid-Promoted Oxidative Cleavage of Carbon-Carbon Bonds: Synthesis of N-Arylated Lactam-Type Iminosugars","volume":"89","author":"Cui","year":"2024","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib13","doi-asserted-by":"crossref","first-page":"5497","DOI":"10.1039\/C6CC01564F","article-title":"Glycomimetic-based pharmacological chaperones for lysosomal storage disorders: lessons from gaucher, GM1-gangliosidosis and Fabry diseases","volume":"52","author":"S\u00e1nchez-Fern\u00e1ndez","year":"2016","journal-title":"Chem. Commun."},{"key":"10.1016\/j.carres.2025.109742_bib14","doi-asserted-by":"crossref","DOI":"10.1016\/j.bioorg.2020.103740","article-title":"Glucocerebrosidase (GCase) activity modulation by 2-alkyl trihydroxypiperidines: inhibition and pharmacological chaperoning","volume":"98","author":"Clemente","year":"2020","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib15","doi-asserted-by":"crossref","first-page":"12745","DOI":"10.1021\/acs.joc.1c01308","article-title":"Piperidine azasugars bering lipophilic chains: stereoselective synthesis and biological activity as inhibitors of glucocerebrosidase (Gcase)","volume":"86","author":"Clemente","year":"2021","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib16a","doi-asserted-by":"crossref","first-page":"77","DOI":"10.2174\/187152008783330851","article-title":"Natural and Synthetic Iminosugars as Carbohydrate Processing Enzyme Inhibitors for Cancer Therapy","volume":"8","author":"Wrodnigg","year":"2008","journal-title":"Anti Cancer Agents Med. Chem."},{"key":"10.1016\/j.carres.2025.109742_bib16b","doi-asserted-by":"crossref","first-page":"84","DOI":"10.3390\/ph12020084","article-title":"Developments in Carbohydrate-Based Cancer Therapeutics","volume":"12","author":"Hossain","year":"2019","journal-title":"Pharmaceuticals"},{"key":"10.1016\/j.carres.2025.109742_bib17a","first-page":"6285","article-title":"Evidence that high mannose glycopeptides are able to functionally interact with recombinant tumor necrosis factor and recombinant interleukin 1","volume":"50","author":"Muchmore","year":"1990","journal-title":"Cancer Res."},{"key":"10.1016\/j.carres.2025.109742_bib17b","first-page":"161","article-title":"Inhibition of human ovarian carcinoma cell\u2012 and hexosaminidase\u2012 mediated degradation of extracellular matrix by sugar analogs","volume":"12","author":"Woynarowska","year":"1992","journal-title":"Anticancer Res."},{"key":"10.1016\/j.carres.2025.109742_bib17c","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1111\/j.1349-7006.1995.tb02986.x","article-title":"Inhibition of Pulmonary Metastases and Tumor Cell Invasion in Experimental Tumors by Sodium D-Glucaro-\u03b4-Lactam (ND2001)","volume":"86","author":"Tsuruoka","year":"1995","journal-title":"Jpn. J. Cancer Res."},{"key":"10.1016\/j.carres.2025.109742_bib17d","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/0008-6215(96)00052-3","article-title":"A practical synthesis from siastatin B of (3S,4S,5R,6R)-4,5-dihydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid having antimetastatic activity in mice","volume":"286","author":"Satoh","year":"1996","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.carres.2025.109742_bib17e","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1007\/s10719-009-9276-3","article-title":"Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives","volume":"27","author":"Padr\u00f3","year":"2010","journal-title":"Glycoconj. J."},{"key":"10.1016\/j.carres.2025.109742_bib18","doi-asserted-by":"crossref","DOI":"10.1016\/j.tet.2021.132380","article-title":"A straightforward approach toward cytotoxic pyrrolidine alkaloids: novel analogues of natural broussonetines","volume":"96","author":"F\u00e1bianov\u00e1","year":"2021","journal-title":"Tetrahedron"},{"key":"10.1016\/j.carres.2025.109742_bib19","article-title":"Stereoselective synthesis and anticancer profile of C-alkyl pyrrolidine-diols with a sphingoid base-like backbone","volume":"122","author":"Pon\u010d\u00e1kov\u00e1","year":"2022","journal-title":"Tetrahedron"},{"key":"10.1016\/j.carres.2025.109742_bib20","doi-asserted-by":"crossref","DOI":"10.1016\/j.tet.2024.133843","article-title":"An approach to pyrrolidine-containing sphingomimetics based on L-tartaric acid chiron","volume":"153","author":"\u0160pakov\u00e1 Raschmanov\u00e1","year":"2024","journal-title":"Tetrahedron"},{"key":"10.1016\/j.carres.2025.109742_bib21","doi-asserted-by":"crossref","unstructured":"B. Lopez-Ortega, S.F. Jenkinson, T.D.W. Claridge, G.W.J. Fleet, Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)oxetane-2-carboxylic acid, Tetrahedron: Asymmetry 19 (2008) 976\u2012983, https:\/\/doi.org\/10.1016\/j.tetasy.2008.03.030.","DOI":"10.1016\/j.tetasy.2008.03.030"},{"key":"10.1016\/j.carres.2025.109742_bib22","doi-asserted-by":"crossref","first-page":"8100","DOI":"10.1021\/ja00178a038","article-title":"Enantiomerically pure polyhydroxylated acyliminium ions. Synthesis of the glycosidase inhibitors (\u2012)-swainsonine and (+)-castanospermine","volume":"112","author":"Miller","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.carres.2025.109742_bib23","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"10.1016\/j.carres.2025.109742_bib24","doi-asserted-by":"crossref","first-page":"611","DOI":"10.3390\/plants12030611","article-title":"Screening evaluation of antiproliferative, antimicrobial and antioxidant activity of lichen extracts and secondary metabolites in vitro","volume":"12","author":"Kello","year":"2023","journal-title":"Plants"}],"container-title":["Carbohydrate Research"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0008621525003684?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0008621525003684?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,3,16]],"date-time":"2026-03-16T02:30:41Z","timestamp":1773628241000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0008621525003684"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,1]]},"references-count":43,"alternative-id":["S0008621525003684"],"URL":"https:\/\/doi.org\/10.1016\/j.carres.2025.109742","relation":{},"ISSN":["0008-6215"],"issn-type":[{"value":"0008-6215","type":"print"}],"subject":[],"published":{"date-parts":[[2026,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"A \u2018chiron\u2019 approach to divergent synthesis of 2-C-tridecyl 1-N-iminosugar mimetics and their anticancer profile","name":"articletitle","label":"Article Title"},{"value":"Carbohydrate Research","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.carres.2025.109742","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2025 Elsevier Ltd. All rights are reserved, including those for text and data mining, AI training, and similar technologies.","name":"copyright","label":"Copyright"}],"article-number":"109742"}}