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Volumn 114, Issue 27, 2017, Pages 6954-6959

Synthesis of asymmetrical multiantennary human milk oligosaccharides

Author keywords

Chemoenzymatic synthesis; Glycosyltransferases; Human milk oligosaccharides; Protein glycan interactions

Indexed keywords

BINDING PROTEIN; GLYCAN; GLYCOSYLTRANSFERASE; OLIGOSACCHARIDE;

EID: 85021708795     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1701785114     Document Type: Article
Times cited : (116)

References (40)
  • 1
    • 0033826695 scopus 로고    scopus 로고
    • Oligosaccharides in human milk: Structural, functional, and metabolic aspects
    • Kunz C, Rudloff S, Baier W, Klein N, Strobel S (2000) Oligosaccharides in human milk: Structural, functional, and metabolic aspects. Annu Rev Nutr 20: 699-722.
    • (2000) Annu Rev Nutr , vol.20 , pp. 699-722
    • Kunz, C.1    Rudloff, S.2    Baier, W.3    Klein, N.4    Strobel, S.5
  • 2
    • 84864465909 scopus 로고    scopus 로고
    • Human milk oligosaccharides: Every baby needs a sugar mama
    • Bode L (2012) Human milk oligosaccharides: Every baby needs a sugar mama. Glycobiology 22: 1147-1162.
    • (2012) Glycobiology , vol.22 , pp. 1147-1162
    • Bode, L.1
  • 3
    • 84978374754 scopus 로고    scopus 로고
    • A microbial perspective of human developmental biology
    • Charbonneau MR, et al. (2016) A microbial perspective of human developmental biology. Nature 535: 48-55.
    • (2016) Nature , vol.535 , pp. 48-55
    • Charbonneau, M.R.1
  • 4
    • 84925852624 scopus 로고    scopus 로고
    • Cultivating healthy growth and nutrition through the gut microbiota
    • Subramanian S, et al. (2015) Cultivating healthy growth and nutrition through the gut microbiota. Cell 161: 36-48.
    • (2015) Cell , vol.161 , pp. 36-48
    • Subramanian, S.1
  • 5
    • 84934444685 scopus 로고    scopus 로고
    • Potential anti-inflammatory and anti-infectious effects of human milk oligosaccharides
    • ed Bösze Z (Springer, New York)
    • Kunz C, Rudloff S (2008) Potential anti-inflammatory and anti-infectious effects of human milk oligosaccharides. Bioactive Components of Milk, Advances in Experimental Medicine and Biology, ed Bösze Z (Springer, New York), Vol 606, pp 455-466.
    • (2008) Bioactive Components of Milk, Advances in Experimental Medicine and Biology , vol.606 , pp. 455-466
    • Kunz, C.1    Rudloff, S.2
  • 6
    • 84904904586 scopus 로고    scopus 로고
    • Glycan-dependent viral infection in infants and the role of human milk oligosaccharides
    • Etzold S, Bode L (2014) Glycan-dependent viral infection in infants and the role of human milk oligosaccharides. Curr Opin Virol 7: 101-107.
    • (2014) Curr Opin Virol , vol.7 , pp. 101-107
    • Etzold, S.1    Bode, L.2
  • 7
    • 33846953590 scopus 로고    scopus 로고
    • Protection of the neonate by the innate immune system of developing gut and of human milk
    • Newburg DS, Walker WA (2007) Protection of the neonate by the innate immune system of developing gut and of human milk. Pediatr Res 61: 2-8.
    • (2007) Pediatr Res , vol.61 , pp. 2-8
    • Newburg, D.S.1    Walker, W.A.2
  • 8
    • 84978370544 scopus 로고    scopus 로고
    • Human milk oligosaccharides: The role in the fine-tuning of innate immune responses
    • Kulinich A, Liu L (2016) Human milk oligosaccharides: The role in the fine-tuning of innate immune responses. Carbohydr Res 432: 62-70.
    • (2016) Carbohydr Res , vol.432 , pp. 62-70
    • Kulinich, A.1    Liu, L.2
  • 9
    • 84866142072 scopus 로고    scopus 로고
    • The human milk oligosaccharide disialyllacto-Ntetraose prevents necrotising enterocolitis in neonatal rats
    • Jantscher-Krenn E, et al. (2012) The human milk oligosaccharide disialyllacto-Ntetraose prevents necrotising enterocolitis in neonatal rats. Gut 61: 1417-1425.
    • (2012) Gut , vol.61 , pp. 1417-1425
    • Jantscher-Krenn, E.1
  • 10
    • 81755171687 scopus 로고    scopus 로고
    • The influence of milk oligosaccharides on microbiota of infants: Opportunities for formulas
    • Chichlowski M, German JB, Lebrilla CB, Mills DA (2011) The influence of milk oligosaccharides on microbiota of infants: Opportunities for formulas. Annu Rev Food Sci Technol 2: 331-351.
    • (2011) Annu Rev Food Sci Technol , vol.2 , pp. 331-351
    • Chichlowski, M.1    German, J.B.2    Lebrilla, C.B.3    Mills, D.A.4
  • 11
    • 84887940017 scopus 로고    scopus 로고
    • Identifying human milk glycans that inhibit norovirus binding using surface plasmon resonance
    • Shang J, et al. (2013) Identifying human milk glycans that inhibit norovirus binding using surface plasmon resonance. Glycobiology 23: 1491-1498.
    • (2013) Glycobiology , vol.23 , pp. 1491-1498
    • Shang, J.1
  • 12
    • 84975127338 scopus 로고    scopus 로고
    • Human DC-SIGN binds specific human milk glycans
    • Noll AJ, et al. (2016) Human DC-SIGN binds specific human milk glycans. Biochem J 473: 1343-1353.
    • (2016) Biochem J , vol.473 , pp. 1343-1353
    • Noll, A.J.1
  • 13
    • 84871757404 scopus 로고    scopus 로고
    • Functional glycomic analysis of humanmilk glycans reveals the presence of virus receptors and embryonic stem cell biomarkers
    • Yu Y, et al. (2012) Functional glycomic analysis of humanmilk glycans reveals the presence of virus receptors and embryonic stem cell biomarkers. J Biol Chem 287: 44784-44799.
    • (2012) J Biol Chem , vol.287 , pp. 44784-44799
    • Yu, Y.1
  • 14
    • 85008040026 scopus 로고
    • Chemical modification of lactose. 13. Synthesis of lacto-N-tetraose
    • Takamura T, Chiba T, Ishihara H, Tejima S (1980) Chemical modification of lactose. 13. Synthesis of lacto-N-tetraose. Chem Pharm Bull (Tokyo) 28: 1804-1809.
    • (1980) Chem Pharm Bull (Tokyo) , vol.28 , pp. 1804-1809
    • Takamura, T.1    Chiba, T.2    Ishihara, H.3    Tejima, S.4
  • 15
    • 0019475704 scopus 로고
    • Chemical modification of lactose. 16. Synthesis of lacto-N-neohexaose
    • Takamura T, Chiba T, Tejima S (1981) Chemical modification of lactose. 16. Synthesis of lacto-N-neohexaose. Chem Pharm Bull (Tokyo) 29: 587-590.
    • (1981) Chem Pharm Bull (Tokyo) , vol.29 , pp. 587-590
    • Takamura, T.1    Chiba, T.2    Tejima, S.3
  • 16
    • 0035177204 scopus 로고    scopus 로고
    • Complex structures of antennary human milk oligosaccharides - Synthesis of a branched octasaccharide
    • Knuhr P, Castro-Palomino J, Grathwohl M, Schmidt RR (2001) Complex structures of antennary human milk oligosaccharides - Synthesis of a branched octasaccharide. Eur J Org Chem 2001: 4239-4246.
    • (2001) Eur J Org Chem , vol.2001 , pp. 4239-4246
    • Knuhr, P.1    Castro-Palomino, J.2    Grathwohl, M.3    Schmidt, R.R.4
  • 17
    • 0035861697 scopus 로고    scopus 로고
    • Solid-phase synthesis of a branched hexasaccharide using a highly efficient synthetic strategy
    • Roussel F, Takhi M, Schmidt RR (2001) Solid-phase synthesis of a branched hexasaccharide using a highly efficient synthetic strategy. J Org Chem 66: 8540-8548.
    • (2001) J Org Chem , vol.66 , pp. 8540-8548
    • Roussel, F.1    Takhi, M.2    Schmidt, R.R.3
  • 18
    • 84900837038 scopus 로고    scopus 로고
    • One-pot glycosylations in the synthesis of human milk oligosaccharides
    • Jennum CA, Fenger TH, Bruun LM, Madsen R (2014) One-pot glycosylations in the synthesis of human milk oligosaccharides. Eur J Org Chem 2014: 3232-3241.
    • (2014) Eur J Org Chem , vol.2014 , pp. 3232-3241
    • Jennum, C.A.1    Fenger, T.H.2    Bruun, L.M.3    Madsen, R.4
  • 19
    • 84903301857 scopus 로고    scopus 로고
    • Synthetic disialyl hexasaccharides protect neonatal rats from necrotizing enterocolitis
    • Yu H, et al. (2014) Synthetic disialyl hexasaccharides protect neonatal rats from necrotizing enterocolitis. Angew Chem Int Ed Engl 53: 6687-6691.
    • (2014) Angew Chem Int Ed Engl , vol.53 , pp. 6687-6691
    • Yu, H.1
  • 20
    • 84928138303 scopus 로고    scopus 로고
    • Sequential one-pot multienzyme (OPME) synthesis of lacto-Nneotetraose and its sialyl and fucosyl derivatives
    • Chen C, et al. (2015) Sequential one-pot multienzyme (OPME) synthesis of lacto-Nneotetraose and its sialyl and fucosyl derivatives. Chem Commun (Camb) 51: 7689-7692.
    • (2015) Chem Commun (Camb) , vol.51 , pp. 7689-7692
    • Chen, C.1
  • 21
    • 84910130416 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of lacto-Ntetrasaccharide and sialyl lacto-N-tetrasaccharides
    • Yao W, Yan J, Chen X, Wang F, Cao H (2015) Chemoenzymatic synthesis of lacto-Ntetrasaccharide and sialyl lacto-N-tetrasaccharides. Carbohydr Res 401: 5-10.
    • (2015) Carbohydr Res , vol.401 , pp. 5-10
    • Yao, W.1    Yan, J.2    Chen, X.3    Wang, F.4    Cao, H.5
  • 22
    • 84978498971 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of a library of human milk oligosaccharides
    • Xiao Z, et al. (2016) Chemoenzymatic synthesis of a library of human milk oligosaccharides. J Org Chem 81: 5851-5865.
    • (2016) J Org Chem , vol.81 , pp. 5851-5865
    • Xiao, Z.1
  • 23
    • 0032192431 scopus 로고    scopus 로고
    • Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates
    • Peri F, Dumy P, Mutter M (1998) Chemo- and stereoselective glycosylation of hydroxylamino derivatives: A versatile approach to glycoconjugates. Tetrahedron 54: 12269-12278.
    • (1998) Tetrahedron , vol.54 , pp. 12269-12278
    • Peri, F.1    Dumy, P.2    Mutter, M.3
  • 24
    • 79959464070 scopus 로고    scopus 로고
    • Glycan microarrays for decoding the glycome
    • Rillahan CD, Paulson JC (2011) Glycan microarrays for decoding the glycome. Annu Rev Biochem 80: 797-823.
    • (2011) Annu Rev Biochem , vol.80 , pp. 797-823
    • Rillahan, C.D.1    Paulson, J.C.2
  • 25
    • 85021724046 scopus 로고    scopus 로고
    • Fucosyltransferase 5. GDP-fucose lactosamine a3/4-fucosyltransferase (FUT5)
    • eds Taniguchi N, et al. (Springer, Tokyo
    • Kannagi R (2014) Fucosyltransferase 5. GDP-fucose lactosamine a3/4-fucosyltransferase (FUT5). Handbook of Glycosyltransferases and Related Genes, eds Taniguchi N, et al. (Springer, Tokyo), pp 549-558.
    • (2014) Handbook of Glycosyltransferases and Related Genes , pp. 549-558
    • Kannagi, R.1
  • 26
    • 67349258025 scopus 로고    scopus 로고
    • Turning 'sweet' on immunity: Galectin-glycan interactions in immune tolerance and inflammation
    • Rabinovich GA, Toscano MA (2009) Turning 'sweet' on immunity: Galectin-glycan interactions in immune tolerance and inflammation. Nat Rev Immunol 9: 338-352.
    • (2009) Nat Rev Immunol , vol.9 , pp. 338-352
    • Rabinovich, G.A.1    Toscano, M.A.2
  • 27
    • 84857158723 scopus 로고    scopus 로고
    • Galectin-9 induced by dietary synbiotics is involved in suppression of allergic symptoms in mice and humans
    • de Kivit S, et al. (2012) Galectin-9 induced by dietary synbiotics is involved in suppression of allergic symptoms in mice and humans. Allergy 67: 343-352.
    • (2012) Allergy , vol.67 , pp. 343-352
    • De Kivit, S.1
  • 28
    • 18444399246 scopus 로고    scopus 로고
    • Functional analysis of the carbohydrate recognition domains and a linker peptide of galectin-9 as to eosinophil chemoattractant activity
    • Sato M, et al. (2002) Functional analysis of the carbohydrate recognition domains and a linker peptide of galectin-9 as to eosinophil chemoattractant activity. Glycobiology 12: 191-197.
    • (2002) Glycobiology , vol.12 , pp. 191-197
    • Sato, M.1
  • 29
    • 0037136406 scopus 로고    scopus 로고
    • Oligosaccharide specificity of galectins: A search by frontal affinity chromatography
    • Hirabayashi J, et al. (2002) Oligosaccharide specificity of galectins: A search by frontal affinity chromatography. Biochim Biophys Acta 1572: 232-254.
    • (2002) Biochim Biophys Acta , vol.1572 , pp. 232-254
    • Hirabayashi, J.1
  • 30
    • 84864592892 scopus 로고    scopus 로고
    • Functional interaction analysis of GM1-related carbohydrates and Vibrio cholerae toxins using carbohydrate microarray
    • Kim CS, Seo JH, Cha HJ (2012) Functional interaction analysis of GM1-related carbohydrates and Vibrio cholerae toxins using carbohydrate microarray. Anal Chem 84: 6884-6890.
    • (2012) Anal Chem , vol.84 , pp. 6884-6890
    • Kim, C.S.1    Seo, J.H.2    Cha, H.J.3
  • 31
    • 84949895682 scopus 로고    scopus 로고
    • Fucosylation and protein glycosylation create functional receptors for cholera toxin
    • Wands AM, et al. (2015) Fucosylation and protein glycosylation create functional receptors for cholera toxin. eLife 4: E09545.
    • (2015) ELife , vol.4 , pp. e09545
    • Wands, A.M.1
  • 33
    • 58249118009 scopus 로고    scopus 로고
    • Sialic acid dependence in rotavirus host cell invasion
    • Haselhorst T, et al. (2009) Sialic acid dependence in rotavirus host cell invasion. Nat Chem Biol 5: 91-93.
    • (2009) Nat Chem Biol , vol.5 , pp. 91-93
    • Haselhorst, T.1
  • 34
    • 80855132554 scopus 로고    scopus 로고
    • Novel structural insights into rotavirus recognition of ganglioside glycan receptors
    • Yu X, et al. (2011) Novel structural insights into rotavirus recognition of ganglioside glycan receptors. J Mol Biol 413: 929-939.
    • (2011) J Mol Biol , vol.413 , pp. 929-939
    • Yu, X.1
  • 35
    • 85070592713 scopus 로고    scopus 로고
    • Safety of 2'-O-fucosyllactose as a novel food ingredient pursuant to Regulation (EC) No 258/97
    • EFSA Panel on Dietetic Products, Nutrition and Allergies
    • EFSA Panel on Dietetic Products, Nutrition and Allergies (2015) Safety of 2'-O-fucosyllactose as a novel food ingredient pursuant to Regulation (EC) No 258/97. EFSA J 13: 4184.
    • (2015) EFSA J , vol.13 , pp. 4184
  • 36
    • 84910669894 scopus 로고    scopus 로고
    • Structural characterization by multistage mass spectrometry (MSn) of human milk glycans recognized by human rotaviruses
    • Ashline DJ, et al. (2014) Structural characterization by multistage mass spectrometry (MSn) of human milk glycans recognized by human rotaviruses. Mol Cell Proteomics 13: 2961-2974.
    • (2014) Mol Cell Proteomics , vol.13 , pp. 2961-2974
    • Ashline, D.J.1
  • 37
    • 84910642776 scopus 로고    scopus 로고
    • Human milk contains novel glycans that are potential decoy receptors for neonatal rotaviruses
    • Yu Y, et al. (2014) Human milk contains novel glycans that are potential decoy receptors for neonatal rotaviruses. Mol Cell Proteomics 13: 2944-2960.
    • (2014) Mol Cell Proteomics , vol.13 , pp. 2944-2960
    • Yu, Y.1
  • 38
    • 84880721909 scopus 로고    scopus 로고
    • A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans
    • Wang Z, et al. (2013) A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans. Science 341: 379-383.
    • (2013) Science , vol.341 , pp. 379-383
    • Wang, Z.1
  • 39
    • 34247565506 scopus 로고    scopus 로고
    • Glycan-based interactions involving vertebrate sialic-acid-recognizing proteins
    • Varki A (2007) Glycan-based interactions involving vertebrate sialic-acid-recognizing proteins. Nature 446: 1023-1029.
    • (2007) Nature , vol.446 , pp. 1023-1029
    • Varki, A.1
  • 40
    • 70350000599 scopus 로고    scopus 로고
    • Structural insights into what glycan arrays tell us about how glycan-binding proteins interact with their ligands
    • Taylor ME, Drickamer K (2009) Structural insights into what glycan arrays tell us about how glycan-binding proteins interact with their ligands. Glycobiology 19: 1155-1162.
    • (2009) Glycobiology , vol.19 , pp. 1155-1162
    • Taylor, M.E.1    Drickamer, K.2


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