321907-99-7Relevant academic research and scientific papers
Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid
Deshpande, Sagar,Matei, Marius Febi,Jaiswal, Rakesh,Bassil, Bassem S.,Kortz, Ulrich,Kuhnert, Nikolai
, p. 7298 - 7306 (2016/10/07)
(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.
Efficient synthesis of (-)-methyl 3-epi-shikimate and methyl 3-epi-quinate by one-pot selective protection of trans-1,2-diols
Armesto,Ferrero,Fernandez,Gotor
, p. 8759 - 8762 (2007/10/03)
trans-1,2-Diol protections of shikimic and quinic acids have been achieved by in situ formation of the protecting group (2,2,3,3-tetramethoxybutane). The synthetic utility of the protected derivatives is demonstrated by the preparation of (-)-methyl 3-epi
