[1] HAN S F,COLLINS B E,PAULSON J C.Synthesis of 9-substituted sialicacids as probes for CD22-ligand interactions on B cells[M]∥Frontiers in mordern carbohydrate chemistry.Washington DC:American Chemistry Society,2007:2-14.
[2] 张嘉宁,汪淑晶.唾液酸生物学与人类健康和疾病[J].生命科学,2011,23(7):678-684.
[3] DJANASHVILI K,FRULLANO L,PETERS J A.Molecular recognition of sialic acid end groups by phenylboronates[J].Chemistry,2005,11(13):4010-4018.
[4] TANGVORANUNTAKUL P,GAGNEUX P,DIAZ S,et al.Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid[J].Proc Natl Acad Sci USA,2003,100(21):12045-12050.
[5] MORLEY T J,WITHERS S G.Chemoenzymatic synthesis and enzymatic analysis of 8-modified cytidine monophosphate-sialic acid and sialyl lactose derivatives[J].J Am Chem Soc,2010,132(27):9430-9437.
[6] VARKI A.Sialic acids in human health and disease[J].Trends Mol Med,2008,14(8):351-360.
[7] MATSUMOTO A,SATO N,KATAOKA K,et al.Noninvasive sialic acid detection at cell membrane by using phenylboronic acid modified self-assembled monolayer gold electrode[J].J Am Chem Soc,2009,131(34):12022-12023.
[8] FUKUDA M.Possible roles of tumor-associated carbohydrate antigens[J].Cancer Res,1996,56(10):2237-2244.
[9] BERTOZZI C R,KIESSLING L L.Chemical glycobiology[J].Science,2001,291(5512):2357-2364.
[10] RAMAN R,RAGURAM S,VENKATARAMAN G,et al.Glycomics:an integrated systems approach to structure-function relationships of glycans[J].Nat Methods,2005,2(11):817-824.
[11] RAZ A,MCLELLAN W L,HART I R,et al.Cell surface properties of B16 melanoma variants with differing metastatic potential[J].Cancer Res,1980,40(5):1645-1651.
[12] DOBROSSY L,PAVELIC Z P,BENACKI R J.A correlation between cell surface sialyltransferase,sialic acid,and glycosidase activities and the implantability of B16 murine melanoma[J].Cancer Res,1981,41(6):2262-2266.
[13] PASSANITI A,HART G W.Cell surface sialylation and tumor metastasis.Metastatic potential of B16 melanoma variants correlates with their relative numbers of specific penultimate oligosaccharide structures[J].J Biol Chem,1988,263(16):7591-7603.
[14] SCHAUER R.Chemistry,metabolism,and biological functions of sialic acids[J].Adv Carbohydr Chem Biochem,1982,40(40):131-234.
[15] LACOMBA R,SALCEDO J,ALEGRíA A,et al.Determination of sialic acid and gangliosides in biological samples and dairy products:a review[J].J Pharm Biomed Anal,2010,51(2):346-357.
[16] ROHRER J S.Analyzing sialic acids using high-performance anion-exchange chromatography with pulsed amperometric detection[J].Anal Biochem,2000,283(1):3-9.
[17] SCHAUER R.Analysis of sialic acids[J].Methods Enzymol,1987,138:132-161.
[18] SPICHTIG V,MICHAUD J,AUSTIN S.Determination of sialic acids in milks and milk-based products[J].Anal Biochem,2010,405(1):28-40.
[19] KAKEHI K,SUSAMI A,TAGA A,et al.High-performance capillary electrophoresis of O-glycosidically linked sialic acid-containing oligosaccharides in glycoproteins as their alditol derivatives with low-wavelength UV monitoring[J].J Chromatogr A,1994,680(1):209-215.
[20] LIU H W,LAW WENDELL H T,LEE LAWRENCE C C,et al.Cyclometalated iridium(Ⅲ)bipyridine-phenylboronic acid complexes as bioimaging reagents and luminescent probes for sialic acids[J].Chem Asian J,2017,12(13):1545-1556.
[21] YUAN L,LIN W,SONG J.Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform[J].Chem Commun,2010,46(42):7930-7932.
[22] ELSINGHORST P W,H?RTIG W,GOLDHAMMER S,et al.A gorge-spanning,high-affinity cholinesterase inhibitor to explore β-amyloid plaques[J].Org Biomol Chem,2009,7(19):3940-3946.
[23] LI K T,LIN Y B,YANG D Y.One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multi-component reactions and their molecular switching properties[J].Org Lett,2012,14(5):1190-1193.
[24] OTSUKA H,UCHIMURA E,KOSHINO H,et al.Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid(Neu5Ac)in aqueous solution with varying pH[J].J Am Chem Soc,2003,125(12):3493-3502.
[25] GOPAUL K P,CROOK M A.Sialic acid:a novel marker of cardiovascular disease?[J].Clin Biochem,2006,39(7):667-681.
[26] WU X,LI Z,CHEN X X,et al.Selective sensing of saccharides using simple boronic acids and their aggregates[J].Chem Soc Rev,2013,42(20):8032-8048.[1] HAN S F,COLLINS B E,PAULSON J C.Synthesis of 9-substituted sialicacids as probes for CD22-ligand interactions on B cells[M]∥Frontiers in mordern carbohydrate chemistry.Washington DC:American Chemistry Society,2007:2-14.
[2] 张嘉宁,汪淑晶.唾液酸生物学与人类健康和疾病[J].生命科学,2011,23(7):678-684.
[3] DJANASHVILI K,FRULLANO L,PETERS J A.Molecular recognition of sialic acid end groups by phenylboronates[J].Chemistry,2005,11(13):4010-4018.
[4] TANGVORANUNTAKUL P,GAGNEUX P,DIAZ S,et al.Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid[J].Proc Natl Acad Sci USA,2003,100(21):12045-12050.
[5] MORLEY T J,WITHERS S G.Chemoenzymatic synthesis and enzymatic analysis of 8-modified cytidine monophosphate-sialic acid and sialyl lactose derivatives[J].J Am Chem Soc,2010,132(27):9430-9437.
[6] VARKI A.Sialic acids in human health and disease[J].Trends Mol Med,2008,14(8):351-360.
[7] MATSUMOTO A,SATO N,KATAOKA K,et al.Noninvasive sialic acid detection at cell membrane by using phenylboronic acid modified self-assembled monolayer gold electrode[J].J Am Chem Soc,2009,131(34):12022-12023.
[8] FUKUDA M.Possible roles of tumor-associated carbohydrate antigens[J].Cancer Res,1996,56(10):2237-2244.
[9] BERTOZZI C R,KIESSLING L L.Chemical glycobiology[J].Science,2001,291(5512):2357-2364.
[10] RAMAN R,RAGURAM S,VENKATARAMAN G,et al.Glycomics:an integrated systems approach to structure-function relationships of glycans[J].Nat Methods,2005,2(11):817-824.
[11] RAZ A,MCLELLAN W L,HART I R,et al.Cell surface properties of B16 melanoma variants with differing metastatic potential[J].Cancer Res,1980,40(5):1645-1651.
[12] DOBROSSY L,PAVELIC Z P,BENACKI R J.A correlation between cell surface sialyltransferase,sialic acid,and glycosidase activities and the implantability of B16 murine melanoma[J].Cancer Res,1981,41(6):2262-2266.
[13] PASSANITI A,HART G W.Cell surface sialylation and tumor metastasis.Metastatic potential of B16 melanoma variants correlates with their relative numbers of specific penultimate oligosaccharide structures[J].J Biol Chem,1988,263(16):7591-7603.
[14] SCHAUER R.Chemistry,metabolism,and biological functions of sialic acids[J].Adv Carbohydr Chem Biochem,1982,40(40):131-234.
[15] LACOMBA R,SALCEDO J,ALEGRíA A,et al.Determination of sialic acid and gangliosides in biological samples and dairy products:a review[J].J Pharm Biomed Anal,2010,51(2):346-357.
[16] ROHRER J S.Analyzing sialic acids using high-performance anion-exchange chromatography with pulsed amperometric detection[J].Anal Biochem,2000,283(1):3-9.
[17] SCHAUER R.Analysis of sialic acids[J].Methods Enzymol,1987,138:132-161.
[18] SPICHTIG V,MICHAUD J,AUSTIN S.Determination of sialic acids in milks and milk-based products[J].Anal Biochem,2010,405(1):28-40.
[19] KAKEHI K,SUSAMI A,TAGA A,et al.High-performance capillary electrophoresis of O-glycosidically linked sialic acid-containing oligosaccharides in glycoproteins as their alditol derivatives with low-wavelength UV monitoring[J].J Chromatogr A,1994,680(1):209-215.
[20] LIU H W,LAW WENDELL H T,LEE LAWRENCE C C,et al.Cyclometalated iridium(Ⅲ)bipyridine-phenylboronic acid complexes as bioimaging reagents and luminescent probes for sialic acids[J].Chem Asian J,2017,12(13):1545-1556.
[21] YUAN L,LIN W,SONG J.Ratiometric fluorescent detection of intracellular hydroxyl radicals based on a hybrid coumarin-cyanine platform[J].Chem Commun,2010,46(42):7930-7932.
[22] ELSINGHORST P W,H?RTIG W,GOLDHAMMER S,et al.A gorge-spanning,high-affinity cholinesterase inhibitor to explore β-amyloid plaques[J].Org Biomol Chem,2009,7(19):3940-3946.
[23] LI K T,LIN Y B,YANG D Y.One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multi-component reactions and their molecular switching properties[J].Org Lett,2012,14(5):1190-1193.
[24] OTSUKA H,UCHIMURA E,KOSHINO H,et al.Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid(Neu5Ac)in aqueous solution with varying pH[J].J Am Chem Soc,2003,125(12):3493-3502.
[25] GOPAUL K P,CROOK M A.Sialic acid:a novel marker of cardiovascular disease?[J].Clin Biochem,2006,39(7):667-681.
[26] WU X,LI Z,CHEN X X,et al.Selective sensing of saccharides using simple boronic acids and their aggregates[J].Chem Soc Rev,2013,42(20):8032-8048.