Lactone-Facilitated Chemoenzymatic Synthesis of Sulfoglucuronosyl Paragloboside Oligosaccharides Bearing the HNK-1 Epitope
Herein, we describe a lactone-facilitated chemoenzymatic strategy for the synthesis of sulfoglucuronosyl paragloboside pentasaccharide, sulfoglucuronosyl lactosaminylparagloboside heptasaccharide, and their nonsulfated derivatives. The approach involves the efficient enzymatic modular assembly (EMA) of the nonsulfated paragloboside backbones, followed by highly regioselective chemical manipulation steps that introduce a sulfate group at the C3 position of glucuronic acid through the formation of a C6,3-lactone intermediate.
Authors
- Song Yu (ORCID: https://orcid.org/0000-0001-5693-7773)
- Na Lu (ORCID: https://orcid.org/0009-0006-0801-5057)
- Hongzhi Cao (ORCID: https://orcid.org/0000-0003-4736-3143)
- Wenlong Yao (ORCID: https://orcid.org/0000-0002-9263-294X)
- Yangyang Liu (ORCID: https://orcid.org/0000-0002-8732-677X)
- Meichao Cai
- Xichao Wang
- Tian Gao (ORCID: https://orcid.org/0009-0003-9855-9071)
- Linlin Sun (ORCID: https://orcid.org/0000-0003-3498-7686)
- Rong Rong (ORCID: https://orcid.org/0000-0001-6261-9202)
Institutions
- Qingdao University (CN)
- Shandong University of Traditional Chinese Medicine (CN)
- Shandong University (CN)
- Peking University (CN)
- Laboratory of Molecular Genetics (PL)
- Institute of Experimental Physics of the Slovak Academy of Sciences (SK)
- BioMimetic Systems (United States) (US)
- Chinese Journal of Integrated Traditional and Western Medicine (CN)
- Ministry of Education (BD)
- Shandong Maternal and Child Health Hospital (CN)
- Qingdao Women and Children's Hospital (CN)
- State Key Laboratory of Natural and Biomimetic Drugs (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c04620
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00