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Gold(I)-Catalyzed 2-Deoxy-β-glycosylation via 1,2-Alkyl/Arylthio Migration: Synthesis of Velutinoside A Pentasaccharide.
J Am Chem Soc
January 2025
Molecular Synthesis Center, Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
2-Deoxy-β-glycosides are essential components of natural products and pharmaceuticals; however, the corresponding 2-deoxy-β-glycosidic bonds are challenging to chemically construct. Herein, we describe an efficient catalytic protocol for synthesizing 2-deoxy-β-glycosides via either IPrAuNTf-catalyzed activation of a unique 1,2--positioned C2--propargyl xanthate (OSPX) leaving group or (PhO)PAuNTf-catalyzed activation of a 1,2--C2--alkynylbenzoate (OABz) substituent of the corresponding thioglycosides. These activation processes trigger 1,2-alkyl/arylthio-migration glycosylation, enabling the synthesis of structurally diverse 2-deoxy-β-glycosides under mild reaction conditions.
View Article and Find Full Text PDFUnderlying Mechanisms of Chromatographic H/D, H/F, and Isomerism Effects in GC-MS.
Metabolites
January 2025
Institute of Toxicology, Core Unit Proteomics, Hannover Medical School, 30623 Hannover, Germany.
Charge-free gaseous molecules labeled with deuterium H (D) atoms elute earlier than their protium-analogs H (H) from most stationary GC phases. This effect is known as the chromatographic H/D isotope effect (IE) and can be calculated by dividing the retention times () of the protiated ( ) to those of the deuterated () analytes: IE = /. Analytes labeled with C, N or O have almost identical retention times and lack a chromatographic isotope effect.
View Article and Find Full Text PDFMethyl Syringate Monoglucoside Is a Crucial Intermediate in Leptosperin Biosynthesis in (ma̅nuka).
J Agric Food Chem
January 2025
Faculty of Health and Nutrition, Shubun University, Ichinomiya, Aichi 491-0938, Japan.
Leptosperin (methyl syringate-4--β-d-gentiobioside) serves as a unique marker for ma̅nuka honey, derived from the ma̅nuka plant (). Despite its importance, the biosynthesis pathway of leptosperin remains unreported. This study investigates the molecular mechanism of leptosperin formation from its aglycone, methyl syringate (MSYR), in ma̅nuka plants.
View Article and Find Full Text PDFDeuterated Nanopolymers for Renal and Lymphatic Imaging via Quantitative Deuterium MRI.
Nano Lett
January 2025
NMR Signal Enhancement Group, Max Planck Institute for Multidisciplinary Sciences, 37077 Göttingen, Germany.
Deuterium (H) MRI is an emerging tool for noninvasive imaging. We explore the integration of H MRI with deuterated multifunctional nanopolymers for deuterated particle imaging (DPI). To this end, amine-terminated G5-polyamidoamine (PAMAM) dendrimers were labeled with deuterated acetyl surface groups, leading to highly H-loaded bioparticles, making them ideal for imaging studies.
View Article and Find Full Text PDFRigorous Analysis of Multimodal HDX-MS Spectra.
J Am Soc Mass Spectrom
January 2025
Department of Medicinal Chemistry, University of Washington, Seattle, Washington 98195, United States.
An inherent strength of hydrogen/deuterium exchange coupled to mass spectrometry (HDX-MS) is its ability to detect the presence of multiple conformational states of a protein, which often manifest as multimodal isotopic envelopes. However, the statistical considerations for accurate analysis of multimodal spectra have yet to be established. Here we outline an unrestrained binomial distribution fitting approach with the corresponding statistical tests to accurately detect and, when possible, deconvolute isotopic distributions that contain multiple subpopulations.
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