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<p>Rare sugars have gained attention as potential raw materials for pharmaceuticals and functional foods. Photocatalysis presents a promising approach for rare sugar synthesis due to its mild reaction conditions and environmental compatibility. While previous photocatalytic methods reported individual routes for specific rare sugars, systematic synthesis through a unified methodology has not been achieved, and control of optical isomers remains insufficiently explored. This study investigated a comprehensive photocatalytic approach for the systematic conversion of monosaccharides with stereochemical configuration preservation. When <span>d</span>-glucose in aqueous solution underwent photocatalytic treatment under UV irradiation, <span>d</span>-arabinose formation was confirmed through HPLC, LCMS, and ¹H NMR analyses. Similarly, <span>d</span>-lyxose, <span>d</span>-ribose, and <span>d</span>-xylose were produced from <span>d</span>-galactose, <span>d</span>-allose, and <span>d</span>-gulose, respectively. Further photocatalytic treatment of these aldopentoses yielded corresponding aldotetroses—<span>d</span>-erythrose from <span>d</span>-ribose and <span>d</span>-arabinose, and <span>d</span>-threose from <span>d</span>-lyxose and <span>d</span>-xylose. This demonstrated successful systematic conversion from aldohexoses to aldopentoses and subsequently to aldotetroses in a single reaction system. Moreover, when <span>l</span>-glucose and <span>l</span>-arabinose were used as starting materials, <span>l</span>-arabinose and <span>l</span>-erythrose were obtained, respectively, confirming stereochemical configuration preservation throughout the conversion process. This method provides a systematic approach for rare sugar synthesis while controlling stereochemical configurations.</p>

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Systematic synthesis of rare sugars and stereospecific conversion via photocatalysis

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月28日

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  • Pratiksha Babgonda Patil,
  • Sho Usuki,
  • Naoko Taki,
  • Yuma Uesaka,
  • Sanjay S. Latthe,
  • Shanhu Liu,
  • Kenji Yamatoya,
  • Kazuya Nakata

摘要

Rare sugars have gained attention as potential raw materials for pharmaceuticals and functional foods. Photocatalysis presents a promising approach for rare sugar synthesis due to its mild reaction conditions and environmental compatibility. While previous photocatalytic methods reported individual routes for specific rare sugars, systematic synthesis through a unified methodology has not been achieved, and control of optical isomers remains insufficiently explored. This study investigated a comprehensive photocatalytic approach for the systematic conversion of monosaccharides with stereochemical configuration preservation. When d-glucose in aqueous solution underwent photocatalytic treatment under UV irradiation, d-arabinose formation was confirmed through HPLC, LCMS, and ¹H NMR analyses. Similarly, d-lyxose, d-ribose, and d-xylose were produced from d-galactose, d-allose, and d-gulose, respectively. Further photocatalytic treatment of these aldopentoses yielded corresponding aldotetroses—d-erythrose from d-ribose and d-arabinose, and d-threose from d-lyxose and d-xylose. This demonstrated successful systematic conversion from aldohexoses to aldopentoses and subsequently to aldotetroses in a single reaction system. Moreover, when l-glucose and l-arabinose were used as starting materials, l-arabinose and l-erythrose were obtained, respectively, confirming stereochemical configuration preservation throughout the conversion process. This method provides a systematic approach for rare sugar synthesis while controlling stereochemical configurations.