An Alternative Approach for the Synthesis of Sulfoquinovosyldiacylglycerol

Abstract

Sulfoquinovosyldiacylglycerol (SQDG) is a glycolipid ubiquitously found in photosynthetically active organisms. It has attracted much attention in recent years due to its biological activities. Similarly, the increasing demand for vegan and functional foods has led to a growing interest in micronutrients such as sulfolipids and their physiological influence on human health. To study this influence, reference materials are needed for developing new analytical methods and providing enough material for model studies on the biological activity. However, the availability of these materials is limited by the difficulty to isolate and purify sulfolipids from natural sources and the unavailability of chemical standards on the market. Consequently, an alternative synthetic route for the comprehensive preparation of sulfolipids was established. Here, the synthesis of a sulfolipid with two identical saturated fatty acids is described exemplarily. The method opens possibilities for the preparation of a diverse range of interesting derivatives with different saturated and unsaturated fatty acids.

Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?

“…The filter cake was washed with additional ethanol, and the combined filtrate was dried over Na 2 SO 4 , filtered through cotton, and concentrated under vacuum to afford a crude residue, which was purified by silica gel chromatography (0→10% CH 3 OH in CH 2 Cl 2 ) to give the desired deprotected glycoside. (29). Obtained from the deprotection of compound 9β (15 mg) using the general procedure for desulfurization eluting from silica gel with 10% MeOH/ in CH 2 Cl 2 to give 5.3 mg for a 75% yield, and spectral data consistent with the literature.…”

“…The allyl groups were removed from each of 5a – d by isomerization with 10 mol % of RuCl 2 (PPh 3 ) 3 followed by treatment with catalytic OsO 4 and N -methylmorpholine N -oxide to give the corresponding hemiacetals 6a – d as α:β mixtures. , Finally, the trichloroacetimidate donors 7a – d were obtained by treatment with 5 equiv of Cl 3 CCN and catalytic amount of DBU at 0 °C in the form of α:β mixtures. − …”

“… 24 , 25 Finally, the trichloroacetimidate donors 7a – d were obtained by treatment with 5 equiv of Cl 3 CCN and catalytic amount of DBU at 0 °C in the form of α:β mixtures. 26 − 29 …”

LC-ESI-MS/MS Analysis of Sulfolipids and Galactolipids in Green and Red Lettuce (Lactuca sativa L.) as Influenced by Sulfur Nutrition

“…The internal standard (2- O -hexadecanoyl- d 31 )-1- O -(9Z,12Z,15Z-octadecatrienoyl) glycerol 3-(6-deoxy-6-sulfo-β- d -glucopyranoside) (IS; SQDG-846; m / z 846) for the quantification of the sulfolipids was prepared according to Sitz et al [ 71 ], with slight modifications. For the modified preparation of the internal standard, the precursor (3-O-[(2′,3′,4′-tri-O-levulinyl-6′-thioacetyl)-β-d-glucosyl]-(R/S)-glycerol) was esterified successively with α-linolenic acid and palmitic acid- d 31 and the oxidation was performed with H 2 O 2 instead of oxon ® .…”