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Article Abstract

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12415908PMC
http://dx.doi.org/10.3762/bjoc.21.131DOI Listing

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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.

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Article Synopsis
  • The synthesis of vinyl-[1-C]pyruvate has been successfully achieved, leading to the production of C hyperpolarized ethyl-[1-C]pyruvate using a technique called ParaHydrogen Induced Polarization (PHIP).
  • The vinyl-ester was created as a more stable ketal derivative to avoid rapid degradation issues associated with pyruvate.
  • Ethyl-[1-C]pyruvate has demonstrated higher efficiency in transferring spin order from ParaHydrogen protons compared to its allyl-derivative, and it is now viable for in vivo metabolic studies due to achieving a high concentration and sufficient carbon polarization.
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