The galactomannan from Antrodia cinnamomea(AC)is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety.The biological function of its corresponding oligosacchar...The galactomannan from Antrodia cinnamomea(AC)is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety.The biological function of its corresponding oligosaccharide fragments has not been revealed yet.In this study,we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation strategy.The preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation,phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro,indicating its immense potential as an immunostimulant candidate.展开更多
Group B Streptococcus(GBS)is the major pathogen that causes invasive infectious diseases in neonates and infants.The develop-ment of preventive and therapeutic strategies against GBS infection has been becoming the mo...Group B Streptococcus(GBS)is the major pathogen that causes invasive infectious diseases in neonates and infants.The develop-ment of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject worldwide.Group B carbohydrate(GBC),the group B-specific polysaccharide that distinguishes GBS with other streptococci species,has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra-antennary structure.In this paper,a highly convergent[3+5]glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligo-saccharide unitⅡhas been developed.In this synthesis,each glycosylation reaction was efficiently constructed with glycosyl im-idates,especially trifluoroacetimidate,as donors,and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2-O-position of imidate donors or the solvent effect of Et_(2)O.Furthermore,the ami-noethylphosphate group was smoothly installed on the 6-O-position of D-glucitoll residue using the phosphoramidite method.After global deprotection,the target octasaccharide was successfully obtained from o-glucitol in 29 steps with an overall yield of 1.37%.The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functional-ized biomolecules for further biological studies.展开更多
The biochemical property and functional identification of three recombinant glycosyltransferases,includingβ-1,4-rhamnosyltransferase(Cps8R),β-1,4-galactosyltransferase(Cps8) and α-2,3-sialyltransferase(Cps8K)involv...The biochemical property and functional identification of three recombinant glycosyltransferases,includingβ-1,4-rhamnosyltransferase(Cps8R),β-1,4-galactosyltransferase(Cps8) and α-2,3-sialyltransferase(Cps8K)involved in the biosynthesis of the tetrasaccharide repeating unit of serotypeⅧcapsular polysaccharide(CPS)of Group B Streptococci(GBS),were systematically investigated.Subsequently,these recombinant enzymes were employed for one-pot three-enzyme efficient synthesis of the tetrasaccharide repeating unit of GBS serotypeⅧCPS using the chemically synthesized Glca-PP-(CH2)ir-OPh as the starting substrate in a satisfying yieldof 87%.展开更多
基金supported by grants from the National Key Research and Development Program of China(No.2018YFA0902000)the National Natural Science Foundation of China(No.21877074).
文摘The galactomannan from Antrodia cinnamomea(AC)is characterized as one of the important bioactive components that exhibits potential immunostimulatory propriety.The biological function of its corresponding oligosaccharide fragments has not been revealed yet.In this study,we reported the first chemical synthesis of the series of oligosaccharide fragments related to AC galactomannan via the convergent glycosylation strategy.The preliminary immunological evaluation of these synthesized AC oligosaccharides disclosed that the backbone tetrasaccharide 1d showed the best immunomodulatory ability on enhancing proliferation,phagocytosis and cytokines secretion of Raw264.7 macrophages in vitro,indicating its immense potential as an immunostimulant candidate.
基金This work was supported by grants from the National Natural Science Foundation of China(Grant number 21877074)the Shandong Provincial Natural Science Foundation(Grant number ZR2019BM007).
文摘Group B Streptococcus(GBS)is the major pathogen that causes invasive infectious diseases in neonates and infants.The develop-ment of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject worldwide.Group B carbohydrate(GBC),the group B-specific polysaccharide that distinguishes GBS with other streptococci species,has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra-antennary structure.In this paper,a highly convergent[3+5]glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligo-saccharide unitⅡhas been developed.In this synthesis,each glycosylation reaction was efficiently constructed with glycosyl im-idates,especially trifluoroacetimidate,as donors,and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2-O-position of imidate donors or the solvent effect of Et_(2)O.Furthermore,the ami-noethylphosphate group was smoothly installed on the 6-O-position of D-glucitoll residue using the phosphoramidite method.After global deprotection,the target octasaccharide was successfully obtained from o-glucitol in 29 steps with an overall yield of 1.37%.The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functional-ized biomolecules for further biological studies.
基金This work was supported by grants from the National Natural Science Foundation of China(Grant numbers 21877074 and 21672129).
文摘The biochemical property and functional identification of three recombinant glycosyltransferases,includingβ-1,4-rhamnosyltransferase(Cps8R),β-1,4-galactosyltransferase(Cps8) and α-2,3-sialyltransferase(Cps8K)involved in the biosynthesis of the tetrasaccharide repeating unit of serotypeⅧcapsular polysaccharide(CPS)of Group B Streptococci(GBS),were systematically investigated.Subsequently,these recombinant enzymes were employed for one-pot three-enzyme efficient synthesis of the tetrasaccharide repeating unit of GBS serotypeⅧCPS using the chemically synthesized Glca-PP-(CH2)ir-OPh as the starting substrate in a satisfying yieldof 87%.