Chiang Tsun-Yi, Lin Mei-Huei, Chang Chun-Wei, Lee Jinq-Chyi, Wang Cheng-Chung
Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.
Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli Country 35053, Taiwan.
Beilstein J Org Chem. 2025 Aug 21;21:1671-1677. doi: 10.3762/bjoc.21.131. eCollection 2025.
Pyruvate ketal is a biologically essential moiety due to its key role as an intermediate in metabolic pathways, serving as a key precursor for the synthesis of various essential biomolecules in organisms. However, the / stereochemistry of pyruvate ketal is difficult to control through chemical methods. In this study, the acid-labile pyruvate ketal linked to the 4- and 6-positions of galactose was cautiously constructed, and the X-ray analysis of the -configured product was successfully obtained. Subsequently, the compound was used for the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor, and a clear structural elucidation was applied by using nuclear magnetic resonance and X-ray.
丙酮酸缩酮是一种生物学上必不可少的部分，因为它作为代谢途径中的中间体发挥着关键作用，是生物体中各种必需生物分子合成的关键前体。然而，丙酮酸缩酮的立体化学很难通过化学方法控制。在本研究中，谨慎构建了与半乳糖的4位和6位相连的酸不稳定型丙酮酸缩酮，并成功获得了该构型产物的X射线分析结果。随后，该化合物被用于合成两性离子多糖A1（PS A1）前体，并通过核磁共振和X射线进行了清晰的结构解析。
