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.

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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

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article

Regio- and Stereoselective Synthesis of the Biotin-Conjugated Keratan Sulfate Hexa- and Octasaccharides [-3)βGal6S(1–4)βGlcNAc6S(1-] 3and4 in the Repeating Disaccharide Region

Naoko Takeda‐Okuda, Jun‐ichi Tamura, Mizuki Yokono, Toshifumi Mizuta et al.
The Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
article

Regio- and Stereoselective Synthesis of the Biotin-Conjugated Keratan Sulfate Hexa- and Octasaccharides [-3)βGal6S(1–4)βGlcNAc6S(1-] 3and4 in the Repeating Disaccharide Region

Naoko Takeda‐Okuda, Jun‐ichi Tamura, Mizuki Yokono, Toshifumi Mizuta, Yuna Uemura, Rei Hattori, Chiaki Iwama
article en

Abstract

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.

The Journal of Organic Chemistry
Sustainability Institute (ZA), Tottori University (JP)
Japan Agency for Medical Research and Development, Ministry of Education, Culture, Sports, Science and Technology
Openalex Percentile: Top 13%
Carbohydrate Chemistry and Synthesis
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