{
  "abstract": "Methylene and difluoromethylene uridine bisphosphonate carbagalactose were designed and synthesized as stable uridine diphosphate-galactose (UDP-Gal) mimics for probing α-1,4-galactosyltransferase (A4GALT). In these analogues, the labile glycosidic and pyrophosphate linkages of UDP-Gal are replaced by chemically and enzymatically stable motifs, yielding compounds that retain key structural features essential for biological recognition. This work demonstrates the first successful nucleophilic substitution of a secondary triflate with a difluoromethylene bisphosphonate, providing a methodology that should enable efficient access to a range of sugar nucleotide mimics. The CH2 and CF2 UDP-Gal analogues 5 and 6 inhibited A4GALT, displaying IC50 values of 249 and 217 μM, respectively, in the presence of 500 μM UDP-Gal, consistent with efficient recognition by the A4GALT donor-binding site.",
  "abstract_shown": true,
  "affiliations": [
    "Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CCLeiden, Netherlands."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 10,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Jianyun Guo",
      "orcid": "0009-0009-9252-7515"
    },
    {
      "affs": [
        0
      ],
      "name": "Nicky de Koster"
    },
    {
      "affs": [
        0
      ],
      "name": "Bob van Puffelen"
    },
    {
      "affs": [
        0
      ],
      "name": "Roy Steneker"
    },
    {
      "affs": [
        0
      ],
      "name": "Vincent Verhoeks",
      "orcid": "0009-0003-4144-0619"
    },
    {
      "affs": [
        0
      ],
      "name": "Tim P Ofman"
    },
    {
      "affs": [
        0
      ],
      "name": "Herman S Overkleeft",
      "orcid": "0000-0001-6976-7005"
    },
    {
      "affs": [
        0
      ],
      "name": "Marta Artola",
      "orcid": "0000-0002-3051-3902"
    },
    {
      "affs": [
        0
      ],
      "name": "Dmitri V Filippov"
    },
    {
      "affs": [
        0
      ],
      "name": "Jeroen D C Codée",
      "orcid": "0000-0003-3531-2138"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/52kpk0mx4r3f6.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.orglett.6c03808",
  "fulltext_url": "https://europepmc.org/articles/PMC13682203",
  "id": "52kpk0mx4r3f6",
  "issns": [
    "1523-7060",
    "1523-7052"
  ],
  "landing_url": "https://europepmc.org/article/MED/42917714",
  "language": "eng",
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Carbohydrate Chemistry and Synthesis"
    ]
  ],
  "openalex": "W7216153053",
  "pdf_url": "https://europepmc.org/articles/PMC13682203?pdf=render",
  "pmcid": "PMC13682203",
  "pmid": "42917714",
  "published": "2026-10-01",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/52kpk0mx4r3f6.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:20:36Z",
      "native_id": "MED:42917714",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42917714"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Carbohydrate Chemistry and Synthesis",
      "subfield": "organic"
    }
  ],
  "title": "Uridine Bisphosphonate-Carbagalactose: A Stabilized α-1,4-Galactosyltransferase Inhibitor.",
  "title_text": "Uridine Bisphosphonate-Carbagalactose: A Stabilized α-1,4-Galactosyltransferase Inhibitor.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:20:36Z",
  "url": "https://research.draconitic.com/paper/52kpk0mx4r3f6",
  "venue": "Organic letters",
  "versions": []
}