唾液酸苷酶的催化机理及水解与合成寡糖进展
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摘要
唾液酸苷酶(EC.3.2.1.18)是一类重要的糖苷水解酶,在动物和微生物中广泛存在.该类酶催化寡糖或糖缀合物上非还原末端唾液酸水解,具有重要的生物学功能,如参与溶酶体降解代谢物、癌症发生、微生物致病等多种生理和病理过程.除了水解活性外,有的唾液酸苷酶还具有转糖基活性,能够以唾液酸单糖或糖苷为糖基供体,催化唾液酸转移到受体分子上,一步合成寡糖和糖苷化合物.这种合成活性对于唾液酸相关糖链的大量获得具有重要意义,有利于推动该类寡糖的基础研究及其在食品和医药中的应用.本文综述了唾液酸苷酶的结构和催化机理、生理功能、转糖基作用及其在寡糖合成中的应用.
ialidases(EC.3.2.1.18) are an important class of glycosidases that are widely found in animals and microorganisms. These enzymes catalyze the cleavage of the terminal sialic acid from various oligosaccharides and sialoglycoconjugates, and play important roles in diverse biological processes such as lysosomal catabolism,tumorigenesis and microbial pathogenesis. Generally, sialidases cleave glycosidic linkages. Under appropriate reaction conditions in vitro, however, the enzymes can catalyze the formation of the glycosidic linkages by transglycosylation reaction. This synthesis activity is important for the large acquisition of sialosides, which would be helpful to promote the basic research on their functions as well as their applications in food and pharmaceutical industries. This paper reviews the structure and catalytic mechanism of sialidases, physiological function, transglycosylation and their application in oligosaccharide synthesis.
ialidases(EC.3.2.1.18) are an important class of glycosidases that are widely found in animals and microorganisms. These enzymes catalyze the cleavage of the terminal sialic acid from various oligosaccharides and sialoglycoconjugates, and play important roles in diverse biological processes such as lysosomal catabolism,tumorigenesis and microbial pathogenesis. Generally, sialidases cleave glycosidic linkages. Under appropriate reaction conditions in vitro, however, the enzymes can catalyze the formation of the glycosidic linkages by transglycosylation reaction. This synthesis activity is important for the large acquisition of sialosides, which would be helpful to promote the basic research on their functions as well as their applications in food and pharmaceutical industries. This paper reviews the structure and catalytic mechanism of sialidases, physiological function, transglycosylation and their application in oligosaccharide synthesis.
引文
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[2]刘志东,王荫榆,郭本恒,等.唾液酸的研究进展.食品工业科技,2010(4):368-373Liu Z D,Wang Y Y,Guo B H,et al.Science and Technology of Food Industry,2010(4):368-373
[3]Schauer R.Achievements and challenges of sialic acid research.Glycoconjugate Journal,2000,17(7-9):485-499
[4]张嘉宁,汪淑晶.唾液酸生物学与人类健康和疾病.生命科学,2011,23(7):678-684Zhang J N,Wang S J.Chinese Bulletin of Life Sciences,2011,23(7):678-684
[5]Kim S,Oh D B,Kang H A,et al.Features and applications of bacterial sialidases.Applied Microbiology&Biotechnology,2011,91(1):1-15
[6]ten Bruggencate S J,Bovee-Oudenhoven I M,Feitsma A L,et al.Functional role and mechanisms of sialyllactose and other sialylated milk oligosaccharides.Nutrition Reviews,2014,72(6):377-389
[7]Warwas M L,Yeung J H,Indurugalla D,et al.Cloning and characterization of a sialidase from the filamentous fungus,Aspergillus fumigatus.Glycoconjugate Journal,2010,27(5):533-548
[8]Taylor G.Sialidases:structures,biological significance and therapeutic potential.Current Opinion in Structural Biology,1996,6(6):830-827
[9]Juge N,Tailford L,Owen C D.Sialidases from gut bacteria:a minireview.Biochemical Society Transactions,2016,44(1):166-175
[10]Schauer R,Kamerling J P.The chemistry and biology of Trypanosomal trans-sialidases:virulence factors in Chagas disease and sleeping sickness.Chem Bio Chem,2011,12(15):2246-2264
[11]Tiralongo E,Schrader S,Lange H,et al.Two trans-sialidase forms with different sialic acid transfer and sialidase activities from Trypanosoma congolense.Journal of Biological Chemistry,2003,278(26):23301-23310
[12]Paris G,Ratier L,Amaya M F,et al.A sialidase mutant displaying trans-sialidase activity.Journal of Molecular Biology,2005,345(4):923-934
[13]Luo Y,Li S C,Chou MY,et al.The crystal structure of an intramolecular trans-sialidase with a Neu Ac alpha 2-3Ga specificity.Structure,1998,6(4):521-530
[14]Gut H,King S J,Walsh M A.Structural and functional studies of Streptococcus pneumoniae neuraminidase B:an intramolecular trans-sialidase.FEBS Letters,2008,582(23-24):3348-3352
[15]Tailford L E,Owen C D,Walshaw J,et al.Discovery of intramolecular trans-sialidases in human gut microbiota suggests novel mechanisms of mucosal adaptation.Nature Communications,2015,6(7624):7624(DOI:10.1038ncomms8624)
[16]Kim S,Oh D B,Kwon O,et al.Identification and functiona characterization of the Nan H extracellular sialidase from Corynebacterium diphtheriae.Journal of Biochemistry,2010147(4):523-533
[17]Cámara M,Boulnois G J,Andrew P W,et al.A neuraminidase from Streptococcus pneumoniae has the features of a surface protein Infection&Immunity,1994,62(9):3688-3695
[18]Xu G,Potter J A,Russell R J,et al.Crystal structure of the Nan Bsialidase from Streptococcus pneumoniae.Journal of Molecular Biology,2008,384(2):436-449
[19]Buschiazzo A,Amaya M F,Cremona M L,et al.The crysta structure and mode of action of trans-sialidase,a key enzyme in Trypanosoma cruzi pathogenesis.Molecular Cell,2002,10(4)757-768
[20]Nordvang R T,Nyffenegger C,Holck J,et al.It all starts with a sandwich:identification of sialidases with trans-glycosylation activity.PLo S One,2016,11(7):e0158434
[21]王亚娟,邢国文.唾液酸酶和唾液酸糖基转移酶的结构、功能与催化反应研究进展.有机化学,2011,31(8):1157-1168Wang Y J,Xing G W.Chinese Journal of Organic Chemistry,201131(8):1157-1168
[22]Gubareva L V,Kaiser L,Hayden F G.Influenza virus neuraminidase inhibitors.Lancet,2000,355(9206):827-835
[23]Roggentin P,Schauer R,Hoyer L L,et al.The sialidase superfamily and its spread by horizontal gene transfer.Molecular Microbiology,1993,9(5):915-921
[24]Corfield T.Bacterial sialidases-roles in pathogenicity and nutrition.Glycobiology,1992,2(6):509-521
[25]Li Y T,Nakagawa H,Ross S A,et al.A novel sialidase which releases 2,7-anhydro-alpha-N-acetylneuraminic acid from sialoglycoconjugates.Journal of Biological Chemistry,1990265(35):21629-21633
[26]Monti E,Preti A,Venerando B,Borsani G.Recent development in mammalian sialidase molecular biology.Neurochemica Research,2002,27(7-8):649-663
[27]Park K H,Kim M G,Ahn H J,et al.Structural and biochemica characterization of the broad substrate specificity of Bacteroides thetaiotaomicron commensal sialidase.Biochimica Et Biophysica Acta Proteins&Proteomics,2013,1834(8):1510-1519
[28]Lee Y,Youn H S,Lee J G,et al.Crystal structure of the catalytic domain of Clostridium perfringens neuraminidase in complex with a non-carbohydrate-based inhibitor,2-(cyclohexylamino)ethanesulfonic acid.Biochemical&Biophysical Research Communications,2017,486(2):470-475
[29]Newstead S L,Potter J A,Wilson J C,et al.The Structure of Clostridium perfringens Nan I sialidase and its catalytic intermediates.Journal of Biological Chemistry,2008,283(14):9080-9088
[30]Roggentin P,Kleineidam R G,Schauer R.Diversity in the properties of two sialidase isoenzymes produced by Clostridium perfringens spp.Biological Chemistry Hoppe-Seyler,1995,376(9):569-576
[31]Aisaka K,Uwajima T.Production of neuraminidase by micromonospora viridifaciens.Fems Microbiology Letters,1987,44(2):289-291
[32]Crennell S J,Garman E F,Laver W G,et al.Crystal structure of a bacterial sialidase(from Salmonella typhimurium LT2)shows the same fold as an influenza virus neuraminidase.Proc Natl Acad Sci U S A,1993,90(21):9852-9856
[33]Owen C D,Lukacik P,Potter J A,et al.Streptococcus pneumoniae Nan C:structural insights into the specificity and mechanism of a sialidase that produces a sialisede inhibitor.Journal of Biological Chemistry,2015,290(46):27736-27748
[34]Crennell S,Garman E,Laver G,et al.Crystal structure of Vibrio cholerae neuraminidase reveals dual lectinlike domains in addition to the catalytic domain.Structure,1994,2(6):535-544
[35]Wilbrink M H,ten Kate G A,van Leeuwen S S,et al.Galactosyllactose sialylation using Trypanosoma cruzi trans-sialidase as the biocatalyst and bovineκ-casein-derived glycomacropeptide as the donor substrate.Applied&Environmental Microbiology,2014,80(19):5984-5991
[36]Pontes-De-Carvalho L C,Tomlinson S,Nussenzweig V.Trypanosoma rangeli,sialidase lacks trans-sialidase activity.Molecular&Biochemical Parasitology,1993,62(1):19-25
[37]PokornáJ,Pachl P,Karlukova E,et al.Kinetic,thermodynamic,and structural analysis of drug resistance mutations in neuraminidase from the 2009 Pandemic Influenza Virus.Viruses,2018,10(7):339-353
[38]Vimr E,Lichtensteiger C.To sialylate,or not to sialylate:that is the question.Trends in Microbiology,2002,10(6):254-257
[39]Vimr E R,Kalivoda K A,Deszo E L,et al.Diversity of microbial sialic acid metabolism.Microbiology&Molecular Biology Reviews,2004,68(1):132-153
[40]Mcguckin M A,Lindén S K,Sutton P,et al.Mucin dynamics and enteric pathogens.Nature Reviews Microbiology,2011,9(4):265-278
[41]Marcobal A,Southwick A M,Earle K A,et al.A refined palate:bacterial consumption of host glycans in the gut.Glycobiology,2013,23(9):1038-1046
[42]Tailford L E,Crost E H,Kavanaugh D,et al.Mucin glycan foraging in the human gut microbiome.Frontiers in Genetics,2015,6(6):81(DOI:10.3389/fgene.2015.00081)
[43]Robinson L S,Lewis W G,Lewis A L.The sialate O-acetylesterase Est A from gut Bacteroidetes species enables sialidase-mediated cross-species foraging of 9-O-acetylated sialoglycans.Journal of Biological Chemistry,2017,292(28):11861-11872
[44]Plumbridge J,Vimr E.Convergent pathways for utilization of the amino sugars,N-acetylglucosamine,N-acetylmannosamine,and N-acetylneuraminic acid by Escherichia coli.Journal of Bacteriology,1999,181(1):47-54
[45]Nakayamaimaohji H,Ichimura M,Iwasa T,et al.Characterization of a gene cluster for sialoglycoconjugate utilization in Bacteroides fragilis.Journal of Medical Investigation,2012,59(1-2):79-94
[46]Marcobal A,Barboza M,Sonnenburg E D,et al.Bacteroides in the infant gut consume milk oligosaccharides via mucus-utilization pathways.Cell Host&Microbe,2011,10(5):507-514
[47]Sebaihia M,Wren B W,Mullany P,et al.The multidrug-resistan human pathogen Clostridium difficile has a highly mobile,mosaic genome.Nature Genetics,2006,38(7):779-786
[48]Vimr E R,Kalivoda K A,Deszo E L,et al.Diversity of microbia sialic acid metabolism.Microbiology and Molecular Biology Reviews,2004,68(1):132-153
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