메뉴 건너뛰기




Volumn 25, Issue 5, 2015, Pages 535-547

Impact of sulfation pattern on the conformation and dynamics of sulfated fucan oligosaccharides as revealed by NMR and MD

Author keywords

conformation; MD; NMR; NOE; oligosaccharides; spin relaxation; sulfated fucan

Indexed keywords

DISACCHARIDE; FUCAN; GLYCAN; OCTASACCHARIDE; OLIGOSACCHARIDE; POLYSACCHARIDE; SULFATE; TETRASACCHARIDE; UNCLASSIFIED DRUG; FUCOIDIN;

EID: 84941073724     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwu184     Document Type: Article
Times cited : (20)

References (36)
  • 1
    • 0022570056 scopus 로고
    • Isolation, fractionation, and preliminary characterization of a novel class of sulfated glycans from the tunic of Styela plicata (Chordata, Tunicata)
    • Albano RM, Mourão PAS. 1986. Isolation, fractionation, and preliminary characterization of a novel class of sulfated glycans from the tunic of Styela plicata (Chordata, Tunicata). J Biol Chem. 261:758-765.
    • (1986) J Biol Chem. , vol.261 , pp. 758-765
    • Albano, R.M.1    Mourão, P.A.S.2
  • 2
    • 0030957599 scopus 로고    scopus 로고
    • Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins
    • Alves AP, Mulloy B, Diniz JA, Mourão PAS. 1997. Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reaction in sperms of sea urchins. J Biol Chem. 272:6965-6971.
    • (1997) J Biol Chem. , vol.272 , pp. 6965-6971
    • Alves, A.P.1    Mulloy, B.2    Diniz, J.A.3    Mourão, P.A.S.4
  • 3
    • 0031706553 scopus 로고    scopus 로고
    • Females of the sea urchin Strongylocentrotus purpuratus differ in the structures of their egg jelly sulfated fucans
    • Alves AP, Mulloy B, Moy GW, Vacquier VD, Mourão PAS. 1998. Females of the sea urchin Strongylocentrotus purpuratus differ in the structures of their egg jelly sulfated fucans. Glycobiology. 8:939-946.
    • (1998) Glycobiology. , vol.8 , pp. 939-946
    • Alves, A.P.1    Mulloy, B.2    Moy, G.W.3    Vacquier, V.D.4    Mourão, P.A.S.5
  • 4
    • 34250859501 scopus 로고    scopus 로고
    • Conformation of sulfated galactan and sulfated fucan in aqueous solutions: Implications to their anticoagulant activities
    • Becker CF, Guimarães JA, Mourão PA, Verli H. 2007. Conformation of sulfated galactan and sulfated fucan in aqueous solutions: Implications to their anticoagulant activities. J Mol Graph Model. 26:391-399.
    • (2007) J Mol Graph Model. , vol.26 , pp. 391-399
    • Becker, C.F.1    Guimarães, J.A.2    Mourão, P.A.3    Verli, H.4
  • 6
    • 4644236600 scopus 로고    scopus 로고
    • Carbohydrate-based species recognition in sea urchin fertilization: Another avenue for speciation?
    • Biermann CH, Marks JA, Vilela-Silva AC, Castro MO, Mourão PA. 2004. Carbohydrate-based species recognition in sea urchin fertilization: Another avenue for speciation? Evol Dev. 6:353-361.
    • (2004) Evol Dev , vol.6 , pp. 353-361
    • Biermann, C.H.1    Marks, J.A.2    Vilela-Silva, A.C.3    Castro, M.O.4    Mourão, P.A.5
  • 8
    • 34547763810 scopus 로고    scopus 로고
    • Expression of two different sulfated fucans by females of Lytechinus variegatus may regulate the seasonal variation in the fertilization of the sea urchin
    • Cinelli LP, Castro MO, Santos LL, Garcia CR, Vilela-Silva ESA-C, Mourão PA. 2007. Expression of two different sulfated fucans by females of Lytechinus variegatus may regulate the seasonal variation in the fertilization of the sea urchin. Glycobiology. 17:877-885.
    • (2007) Glycobiology. , vol.17 , pp. 877-885
    • Cinelli, L.P.1    Castro, M.O.2    Santos, L.L.3    Garcia, C.R.4    Esa-C, V.5    Mourão, P.A.6
  • 10
    • 0022552896 scopus 로고
    • Improved quantification and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue
    • Farndale RW, Buttle DJ, Barret AJ. 1986. Improved quantification and discrimination of sulphated glycosaminoglycans by use of dimethylmethylene blue. Biochim Biophys Acta. 883:173-177.
    • (1986) Biochim Biophys Acta , vol.883 , pp. 173-177
    • Farndale, R.W.1    Buttle, D.J.2    Barret, A.J.3
  • 13
    • 84856688126 scopus 로고    scopus 로고
    • Structure and haemostatic effects of generic versions of LMWHs available for clinical use in Brazil: Similarity to the original drug
    • Glauser BF, Vairo BC, Oliveira SN, Cinelli LP, Pereira MS, Mourão PA. 2012. Structure and haemostatic effects of generic versions of LMWHs available for clinical use in Brazil: similarity to the original drug. Thromb Haemost. 107:302-314.
    • (2012) Thromb Haemost , vol.107 , pp. 302-314
    • Glauser, B.F.1    Vairo, B.C.2    Oliveira, S.N.3    Cinelli, L.P.4    Pereira, M.S.5    Mourão, P.A.6
  • 15
    • 20444483055 scopus 로고
    • The relationship between proton-proton NMR coupling constants and substituent electronegativities-I: An empirical generalization of the Karplus equation
    • Haasnoot CAG, de Leeuw FAAM, Altona C. 1980. The relationship between proton-proton NMR coupling constants and substituent electronegativities-I: An empirical generalization of the Karplus equation. Tetrahedron. 36:2783-2792.
    • (1980) Tetrahedron. , vol.36 , pp. 2783-2792
    • Cag, H.1    De Leeuw FAAM2    Altona, C.3
  • 16
    • 0035845496 scopus 로고    scopus 로고
    • Solvent interactions determine carbohydrate conformation
    • Kirschner KN, Woods RJ. 2001. Solvent interactions determine carbohydrate conformation. Proc Natl Acad Sci USA. 98:10541-10545.
    • (2001) Proc Natl Acad Sci USA. , vol.98 , pp. 10541-10545
    • Kirschner, K.N.1    Woods, R.J.2
  • 18
    • 33846266616 scopus 로고    scopus 로고
    • A carbohydrate-based mechanism of species recognition in sea urchin fertilization
    • Mourão PA. 2007. A carbohydrate-based mechanism of species recognition in sea urchin fertilization. Braz J Med Biol Res. 40:5-17.
    • (2007) Braz J Med Biol Res. , vol.40 , pp. 5-17
    • Mourão, P.A.1
  • 19
    • 0033650826 scopus 로고    scopus 로고
    • Conformations and dynamics of heparin and heparan sulfates
    • Mulloy B, Forster MJ. 2000. Conformations and dynamics of heparin and heparan sulfates. Glycobiology. 10:1147-1156.
    • (2000) Glycobiology. , vol.10 , pp. 1147-1156
    • Mulloy, B.1    Forster, M.J.2
  • 20
    • 0028058899 scopus 로고
    • Sulfated fucans from echinoderms have a regular tetrasaccharide repeating unit defined by specific patterns of sulfation at the O-2 and O-4 positions
    • Mulloy B, Ribeiro AC, Alves AP, Vieira RP, Mourão PA. 1994. Sulfated fucans from echinoderms have a regular tetrasaccharide repeating unit defined by specific patterns of sulfation at the O-2 and O-4 positions. J Chem Biol. 269:22113-22123.
    • (1994) J Chem Biol. , vol.269 , pp. 22113-22123
    • Mulloy, B.1    Ribeiro, A.C.2    Alves, A.P.3    Vieira, R.P.4    Mourão, P.A.5
  • 21
    • 84894268675 scopus 로고    scopus 로고
    • Importance of ligand conformational energies in carbohydrate docking: Sorting the wheat from the chaff
    • Nivedha AK, Makeneni S, Foley BL, Tessier MB, Woods RJ. 2014. Importance of ligand conformational energies in carbohydrate docking: Sorting the wheat from the chaff. J Comput Chem. 35:526-539.
    • (2014) J Comput Chem. , vol.35 , pp. 526-539
    • Nivedha, A.K.1    Makeneni, S.2    Foley, B.L.3    Tessier, M.B.4    Woods, R.J.5
  • 22
    • 69449086436 scopus 로고    scopus 로고
    • Review: An overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures
    • Pomin VH. 2009. Review: An overview about the structure-function relationship of marine sulfated homopolysaccharides with regular chemical structures. Biopolymers. 91:601-609.
    • (2009) Biopolymers. , vol.91 , pp. 601-609
    • Pomin, V.H.1
  • 23
    • 84866673239 scopus 로고    scopus 로고
    • Fucanomics and galactanomics: Current status in drug discovery, mechanism of action and role of the well-defined structures
    • Pomin VH. 2012a. Fucanomics and galactanomics: Current status in drug discovery, mechanism of action and role of the well-defined structures. Biochim Biophys Acta. 1820:1971-1979.
    • (2012) Biochim Biophys Acta , vol.1820 , pp. 1971-1979
    • Pomin, V.H.1
  • 24
    • 84857211730 scopus 로고    scopus 로고
    • Structure-function relationship of anticoagulant and antithrombotic well-defined sulfated polysaccharides from marine invertebrates
    • Pomin VH. 2012b. Structure-function relationship of anticoagulant and antithrombotic well-defined sulfated polysaccharides from marine invertebrates. Adv Food Nutr Res. 65:195-209.
    • (2012) Adv Food Nutr Res. , vol.65 , pp. 195-209
    • Pomin, V.H.1
  • 25
    • 84899060063 scopus 로고    scopus 로고
    • Solution NMR conformation of glycosaminoglycans
    • Pomin VH. 2014a. Solution NMR conformation of glycosaminoglycans. Prog Biophys Mol Biol. 114:61-68.
    • (2014) Prog Biophys Mol Biol , vol.114 , pp. 61-68
    • Pomin, V.H.1
  • 26
    • 84903819687 scopus 로고    scopus 로고
    • Anticoagulant motifs of marine sulfated glycans
    • Pomin VH. 2014b. Anticoagulant motifs of marine sulfated glycans. Glycoconj J. 31:341-344.
    • (2014) Glycoconj J. , vol.31 , pp. 341-344
    • Pomin, V.H.1
  • 27
    • 57149087953 scopus 로고    scopus 로고
    • Structure, biology, evolution, and medical importance of sulfated fucans and galactans
    • Pomin VH, Mourão PA. 2008. Structure, biology, evolution, and medical importance of sulfated fucans and galactans. Glycobiology. 18:1016-1027.
    • (2008) Glycobiology. , vol.18 , pp. 1016-1027
    • Pomin, V.H.1    Mourão, P.A.2
  • 28
    • 84898733367 scopus 로고    scopus 로고
    • Specific sulfation and glycosylation-A structural combination for the anticoagulation of marine carbohydrates
    • Pomin VH, Mourão PA. 2014. Specific sulfation and glycosylation-A structural combination for the anticoagulation of marine carbohydrates. Front Cell Infect Microbiol. 6(3):33.
    • (2014) Front Cell Infect Microbiol. , vol.6 , Issue.3 , pp. 33
    • Pomin, V.H.1    Mourão, P.A.2
  • 29
    • 22444437313 scopus 로고    scopus 로고
    • Selective cleavage and anticoagulant activity of a sulfated fucan: Stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor IIdependent anticoagulant activity
    • Pomin VH, Pereira MS, Valente AP, Tollefsen DM, Pavão MS, Mourão PA. 2005. Selective cleavage and anticoagulant activity of a sulfated fucan: Stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor IIdependent anticoagulant activity. Glycobiology. 15:369-381.
    • (2005) Glycobiology. , vol.15 , pp. 369-381
    • Pomin, V.H.1    Pereira, M.S.2    Valente, A.P.3    Tollefsen, D.M.4    Pavão, M.S.5    Mourão, P.A.6
  • 30
    • 77952472941 scopus 로고    scopus 로고
    • Characterization of glycosaminoglycans by 15N NMR spectroscopy and in vivo isotopic labeling
    • Pomin VH, Sharp JS, Li X, Wang L, Prestegard JH. 2010. Characterization of glycosaminoglycans by 15N NMR spectroscopy and in vivo isotopic labeling. Anal Chem. 82:4078-4088.
    • (2010) Anal Chem. , vol.82 , pp. 4078-4088
    • Pomin, V.H.1    Sharp, J.S.2    Li, X.3    Wang, L.4    Prestegard, J.H.5
  • 31
    • 28444461067 scopus 로고    scopus 로고
    • Mild acid hydrolysis of sulfated fucans: A selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides
    • Pomin VH, Valente AP, Pereira MS, Mourão PA. 2005. Mild acid hydrolysis of sulfated fucans: A selective 2-desulfation reaction and an alternative approach for preparing tailored sulfated oligosaccharides.Glycobiology. 15:1376-1385.
    • (2005) Glycobiology , vol.15 , pp. 1376-1385
    • Pomin, V.H.1    Valente, A.P.2    Pereira, M.S.3    Mourão, P.A.4
  • 32
    • 84946450438 scopus 로고
    • Algorithms for macromolecular dynamics and constraint dynamics
    • Vangunsteren WF, Berendsen HJC. 1977. Algorithms for macromolecular dynamics and constraint dynamics. Mol Phys. 34:1311-1327.
    • (1977) Mol Phys , vol.34 , pp. 1311-1327
    • Vangunsteren, W.F.1    Berendsen, H.J.C.2
  • 33
    • 0032865813 scopus 로고    scopus 로고
    • Structure of the sulfated ?-L-fucan from the egg jelly coat of the sea urchin Strongylocentrotus franciscanus: Patterns of preferential 2-O-and 4-O-sulfation determine sperm cell recognition
    • Vilela-Silva A-CES, Alves AP, Valente AP, Vacquier VD, Mourão PAS. 1999. Structure of the sulfated ?-L-fucan from the egg jelly coat of the sea urchin Strongylocentrotus franciscanus: Patterns of preferential 2-O-and 4-O-sulfation determine sperm cell recognition. Glycobiology. 9:927-933.
    • (1999) Glycobiology. , vol.9 , pp. 927-933
    • A-Ces, V.1    Alves, A.P.2    Valente, A.P.3    Vacquier, V.D.4    Mourão, P.A.S.5
  • 34
    • 0037016675 scopus 로고    scopus 로고
    • Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus droebachiensis and Strongylocentrotus pallidus ensure species-specific fertilization
    • Vilela-Silva A-CES, Castro MO, Valente AP, Biermann CH, Mourão PAS. 2002. Sulfated fucans from the egg jellies of the closely related sea urchins Strongylocentrotus droebachiensis and Strongylocentrotus pallidus ensure species-specific fertilization. J Biol Chem. 277:379-387.
    • (2002) J Biol Chem. , vol.277 , pp. 379-387
    • A-Ces, V.1    Castro, M.O.2    Valente, A.P.3    Biermann, C.H.4    Mourão, P.A.S.5
  • 35
    • 54249094751 scopus 로고    scopus 로고
    • The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization
    • Vilela-Silva A-CES, Hirohashi N, Mourão PA. 2008. The structure of sulfated polysaccharides ensures a carbohydrate-based mechanism for species recognition during sea urchin fertilization. Int J Dev Biol. 52:551-559.
    • (2008) Int J Dev Biol. , vol.52 , pp. 551-559
    • A-Ces, V.1    Hirohashi, N.2    Mourão, P.A.3
  • 36
    • 0027911220 scopus 로고
    • Influence of sulfate and carboxylate groups on the conformation of chondroitin sulfate related disaccharides
    • Zsiska M, Meyer B. 1993. Influence of sulfate and carboxylate groups on the conformation of chondroitin sulfate related disaccharides. Carbohydr Res. 243:225-258.
    • (1993) Carbohydr Res. , vol.243 , pp. 225-258
    • Zsiska, M.1    Meyer, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.