Chemical synthesis of diglucosyl diacylglycerols utilizing glycosyl donors with stereodirecting cyclic silyl protective groups. (1st September 2019)

• Record Type: Journal Article
• Authors: Takato, Koichi; Kurita, Motoki; Yagami, Nahoko; Tanaka, Hide-Nori; Ando, Hiromune; Imamura, Akihiro; Ishida, Hideharu
• Is Part Of: Carbohydrate research. Volume 483(2019)
• Publication Date: 2019-09-01
• Subjects: Diglycosyl diacylglycerol -- Glycosylation -- Stereodirecting -- Stereoselective -- Silyl protective group; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2019.107748
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Chemical syntheses of the bacterial diglucosyl diacylglycerols 1-heptadecanoyl-2-pentadecanoyl-3- O -[6- O -(β-d-glucopyranosyl)-β-d-glucopyranosyl]- sn -glycerol and 1-( cis -13-octadecenoyl)-2-palmitoyl-3- O -[2- O -(α-d-glucopyranosyl)-α-d-glucopyranosyl]- sn -glycerol are described. The syntheses feature the stereoselective construction of glycosidic linkages in glycosylation reaction by utilizing glycosyl donors with stereodirecting cyclic silyl protective groups. The 1, 1, 3, 3-tetraisopropyldisiloxane-1, 3-diyl (TIPDS) group was used for formation of the β-glycosidic linkage, while the di- tert -butylsilylene (DTBS) group was used for α-linkage formation. The silyl protective groups were chemoselectively cleavable without affecting acyl functionalities on the glycerol moiety and proved effective for the synthesis of diacylglycoglycerolipids. Graphical abstract: Image 1 Highlights: Diglucosyl diacylglycerols (DGDGs) occur widely in nature. Efficient chemical syntheses of two representative bacterial DGDGs were achieved. Stereodirecting effects of cyclic silyl protective groups delivered target DGDGs.