Rapid Synthesis of Oversulfated Chondroitin Sulfate

Hiroshi Akiyama; Hiori Misu; Yume Tsuruyama; Sanami Isaka; Utano Makiyama; Mayumi Ikegami-Kawai; Natsuko Miki; Yukari Nakagawa; Hideki Tamura; Yusuke Iwasaki; Rie Ito

doi:10.1248/bpb.b25-00117

Note

Rapid Synthesis of Oversulfated Chondroitin Sulfate

Hiroshi Akiyama , Hiori Misu, Yume Tsuruyama, Sanami Isaka, Utano Makiyama, Mayumi Ikegami-Kawai, Natsuko Miki, Yukari Nakagawa, Hideki Tamura, Yusuke Iwasaki, Rie Ito

Author information

Hiroshi Akiyama Corresponding author
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
National Institute of Health Sciences, 3–25–26 Tonomachi, Kawasaki-ku, Kawasaki 210–9501, Japan
Hiori Misu
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Yume Tsuruyama
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Sanami Isaka
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Utano Makiyama
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Mayumi Ikegami-Kawai
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Natsuko Miki
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Yukari Nakagawa
Pharmaceutical Reference Standards Center, Pharmaceutical and Medical Device Regulatory Science Society of Japan, 2–1–2 Hiranomachi, Chuo-ku, Osaka 541–0046, Japan
Hideki Tamura
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Yusuke Iwasaki
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan
Rie Ito
School of Pharmacy and Pharmaceutical Sciences, Hoshi University, 2–4–41 Ebara, Shinagawa-ku, Tokyo 142–8501, Japan

Keywords: oversulfated chondroitin sulfate, NMR, edited heteronuclear single quantum correlation, synthesis

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Supplementary material

2025 Volume 48 Issue 6 Pages 801-804

DOI https://doi.org/10.1248/bpb.b25-00117

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Abstract

Oversulfated chondroitin sulfate (OSCS) is a chondroitin sulfate ester in which all hydroxyl groups have been converted to sulfuric acid esters. Here, we describe a rapid, novel synthesis method for OSCS. ¹H-NMR analysis revealed that all signals derived from the protons of N-acetyl-galactosamine and glucuronic acid in the synthesized OSCS were shifted downfield due to sulfonation compared with the chondroitin sulfate (CS) starting material. Comparison of the edited heteronuclear single quantum correlation spectrum of the prepared OSCS with that of the Japanese Pharmacopoeia OSCS reference standard showed excellent agreement between the main correlation peaks. The proposed novel synthesis method for OSCS is faster and simpler than the conventional method.

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