We herein reported the first chemoenzymatic synthesis of lacto-N-hexaose (LNH) by combining chemical carbohydrate synthesis with a selectively enzymatic glycosylation strategy. A tetrasaccharide core structure GlcNH2β1→3 (GlcNAcβ1→6) Galβ1→4Glc, a key precursor for subsequent enzymatic glycan extension toward asymmetrically branched human milk oligosaccharides, was synthesized in this work. When the order of galactosyltransferase-catalyzed reactions was appropriately arranged, the β1,4-galactosyl and β1,3-galactosyl moieties could be sequentially assembled on the C6-arm and C3-arm of the tetrasaccharide, respectively, to achieve an efficient LNH synthesis. Lacto-N-neotetraose (LNnH), another common human milk oligosaccharide, was also synthesized en route to the target LNH.
There are two independent 3,5-dimethylpyrazole and two independent 2-hydroxy-5-(phenyldiazenyl)benzoic acid molecules [in which intramolecular O—H⋯O bonds form S(6) graph-set motifs] in the asymmetric unit of the title compound, C5H8N2·C13H10N2O3. In the crystal, the components are linked by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming four-component clusters. Further stabilization is provided by weak C—H⋯π interactions.
Camellia oleifera Abel. (C. oleifera), one of the four woody oil-producing plants in the world produces edible oils with high percentage of unsaturated fatty acid content in seeds. The mature C. oleifera seeds continue to undergo a series of physiological changes after harvest. To this end, the dynamic changes in nutrients, oil content, fatty acid composition, and endogenous hormone content in C. oleifera seeds under different natural drying times after harvest were investigated. The content of soluble sugar and soluble protein of C. oleifera seeds increased with the extension of natural drying, especially soluble sugar content increased nearly 2-fold at 30 d after post-harvest natural drying compared with that of the control group. The content of oil reached a peak (23.6%) at 30 d after post-harvest natural drying. During the post-harvest natural drying process, the relative content of palmitic acid and oleic acid increased, while the relative content of palmitic acid and linoleic acid decreased. Furthermore, the levels of unsaturated fatty acids (oleic acid, linoleic acid, linolenic acid, and arachidonic acid) increased significantly with increasing natural drying time. The overall trend of endogenous hormones SA, SL, and ACC concentrations increased with the post-harvest natural drying process. Furthermore, the concentration of SA, SL, and ACC were positively correlated with oil content. Altogether, post-harvest natural drying for 30 days significantly promoted the anabolism of oil and improved the quality of C. oleifera seeds. These findings provide a scientific basis for reasonable post-harvest treatment to improve Camellia oil yield.
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