Regio- and Stereoselective Synthesis of the Biotin-Conjugated Keratan Sulfate Hexa- and Octasaccharides [-3)βGal6S(1–4)βGlcNAc6S(1-] <sub>3and4</sub> in the Repeating Disaccharide Region
Keratan sulfate (KS) is an acidic linear polysaccharide belonging to the glycosaminoglycan family. The repeating disaccharide unit of KS consists of the sequence -4)-βGlcNAc(1→3)-βGal(1→, with varying sulfation patterns at the primary hydroxy groups. L4 is a subclass of KS in which both primary hydroxy groups are sulfated. Herein, we report an efficient synthesis of KS L4 hexa- and octasaccharides as biotin conjugates through coupling reactions employing partially protected glycosyl acceptors.
Authors
- Naoko Takeda‐Okuda
- Jun‐ichi Tamura (ORCID: https://orcid.org/0000-0002-3957-0479)
- Mizuki Yokono
- Toshifumi Mizuta
- Yuna Uemura
- Rei Hattori
- Chiaki Iwama
Institutions
- Sustainability Institute (ZA)
- Tottori University (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-06-16
- DOI
- https://doi.org/10.1021/acs.joc.6c00722
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development
- Ministry of Education, Culture, Sports, Science and Technology