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嗜盐单胞菌KR26 O-多糖共轭就绪四糖重复单元的合成。

Synthesis of the conjugation ready tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26.

作者信息

Rudra Bijoy, Mukhopadhyay Balaram

机构信息

Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia, 741246, India.

Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia, 741246, India.

出版信息

Carbohydr Res. 2025 Mar;549:109371. doi: 10.1016/j.carres.2024.109371. Epub 2024 Dec 28.

DOI:10.1016/j.carres.2024.109371
PMID:39742801
Abstract

Synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Halomonas fontilapidosi KR26 was accomplished through a convergent [2 + 2]-block strategy using rationally protected monosaccharide synthons derived from commercially available sugars. The target tetrasaccharide was synthesized in the form of its 2-azidoethyl glycoside to ensure further conjugation with specific aglycons without hampering the reducing end stereochemistry. Use of only acyl/aryl protecting groups was targeted to keep the terminal azido-group intact for the utilization of "Click chemistry" for further conjugations.

摘要

利用从市售糖类衍生而来的经过合理保护的单糖合成子,通过收敛性的[2 + 2]砌块策略完成了来自盐单胞菌KR26的O-多糖四糖重复单元的合成。目标四糖以其2-叠氮基乙基糖苷的形式合成,以确保与特定苷元进一步缀合,同时不妨碍还原端的立体化学。仅使用酰基/芳基保护基团的目的是保持末端叠氮基团完整,以便利用“点击化学”进行进一步缀合。

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