Scholarlink

<p>Human milk oligosaccharides (HMOs) have highly diverse and branched structures that present a significant challenge for chemical synthesis. Here we show that masking the amino group in glucosamine with a <i>p</i>-nitrobenzyloxycarbonyl (<i>p</i>NZ) protecting group enhances coupling and deprotection efficiency during automated glycan assembly (AGA) of homogeneous HMOs, including the lacto-<i>N</i>-tetraose (LNT), lacto-<i>N</i>-neotetraose (LNnT), lacto-<i>N</i>-fucopentaose (LNFP), lacto-<i>N</i>-difuco-hexaose (LNDFH), and lacto-N-neohexaose (LNnH) series. Deprotection strategies are developed to achieve excellent purity of linear and branched HMO structures. The end-to-end tractability of <i>p</i>NZ-protected oligosaccharides underscores the robustness of this approach, while three orthogonal deprotection pathways offer synthetic versatility for HMO compounds.</p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

p-nitrobenzyloxycarbonyl protective group as key to automated glycan assembly of neutral human milk oligosaccharides

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年12月5日

查看全文
  • Mei-Huei Lin,
  • Yan-Ting Kuo,
  • Kim Le Mai Hoang,
  • Peter H. Seeberger

摘要

Human milk oligosaccharides (HMOs) have highly diverse and branched structures that present a significant challenge for chemical synthesis. Here we show that masking the amino group in glucosamine with a p-nitrobenzyloxycarbonyl (pNZ) protecting group enhances coupling and deprotection efficiency during automated glycan assembly (AGA) of homogeneous HMOs, including the lacto-N-tetraose (LNT), lacto-N-neotetraose (LNnT), lacto-N-fucopentaose (LNFP), lacto-N-difuco-hexaose (LNDFH), and lacto-N-neohexaose (LNnH) series. Deprotection strategies are developed to achieve excellent purity of linear and branched HMO structures. The end-to-end tractability of pNZ-protected oligosaccharides underscores the robustness of this approach, while three orthogonal deprotection pathways offer synthetic versatility for HMO compounds.