메뉴 건너뛰기




Volumn 22, Issue 1, 2012, Pages 96-106

Directing the biological activities of heparan sulfate oligosaccharides using a chemoenzymatic approach

Author keywords

antithrombin; FGF; heparan sulfate; oligosaccharides; sulfotransferases

Indexed keywords

ANTITHROMBIN; FIBROBLAST GROWTH FACTOR 2; HEPARAN SULFATE; HEPARIN; HEPTASACCHARIDE 2; HEPTASACCHARIDE 3; HEPTASACCHARIDE 4; IDURONIC ACID; NONASACCHARIDE 7; NONASACCHARIDE 8; NONASACCHARIDE 9; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

EID: 83255165450     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwr109     Document Type: Article
Times cited : (23)

References (41)
  • 1
    • 1842530198 scopus 로고    scopus 로고
    • Characterization of Growth Factor-binding Structures in Heparin/Heparan Sulfate Using an Octasaccharide Library
    • DOI 10.1074/jbc.M313523200
    • Ashikari-Hada S, Habuchi H, Kariya Y, Itoh N, Reddi H, Kimata K. 2004. Characterization of the growth factor-binding structures in heparin/heparan sulfate using an octasaccharide library. J Biol Chem. 279:12346-12354. (Pubitemid 38445801)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.13 , pp. 12346-12354
    • Ashikari-Hada, S.1    Habuchi, H.2    Kariya, Y.3    Itoh, N.4    Reddi, A.H.5    Kimata, K.6
  • 2
    • 65849150715 scopus 로고    scopus 로고
    • Specific inhibition of FGF-2 signaling with 2-O-sulfated octasaccharides of heparin sulfate
    • Ashikari-Hada S, Habuchi H, Sugaya N, Kobayashi T, Kimata K. 2009. Specific inhibition of FGF-2 signaling with 2-O-sulfated octasaccharides of heparin sulfate. Glycobiology. 19:644-654.
    • (2009) Glycobiology , vol.19 , pp. 644-654
    • Ashikari-Hada, S.1    Habuchi, H.2    Sugaya, N.3    Kobayashi, T.4    Kimata, K.5
  • 3
    • 0022368634 scopus 로고
    • Contribution of monosaccharide residues in heparin binding to antithrombin III
    • DOI 10.1021/bi00344a063
    • Atha DH, Lormeau J-C, Petitou M, Rosenberg RD, Choay J. 1985. Contribution of monosaccharide residues in heparin binding to antithrombin III. Biochemistry. 24:6723-6729. (Pubitemid 16207156)
    • (1985) Biochemistry , vol.24 , Issue.23 , pp. 6723-6729
    • Atha, D.H.1    Lormeau, J.-C.2    Petitou, M.3
  • 4
    • 0030008364 scopus 로고    scopus 로고
    • An animal cell mutant defective in heparan sulfate hexuronic acid 2-O- sulfation
    • DOI 10.1074/jbc.271.30.17711
    • Bai X, Esko JD. 1996. An animal cell mutant defective in heparan sulfate hexuronic acid 2-O-sulfation. J Biol Chem. 271:17711-17717. (Pubitemid 26250742)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.30 , pp. 17711-17717
    • Bai, X.1    Esko, J.D.2
  • 6
    • 0347379921 scopus 로고    scopus 로고
    • Sulfated Derivatives of Escherichia coli K5 Polysaccharides as Modulators of Fibroblast Growth Factor Signaling
    • DOI 10.1074/jbc.M304208200
    • Borgenstrom M, Jalkanen M, Salmivirta M. 2003. Sulfated derivatives of Escherichia coli K5 polysaccharides as modulators of fibroblast growth factor signaling. J Biol Chem. 278:49882-49889. (Pubitemid 37548823)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.50 , pp. 49882-49889
    • Borgenstrom, M.1    Jalkanen, M.2    Salmivirta, M.3
  • 8
    • 34548615858 scopus 로고    scopus 로고
    • Using an Enzymatic Combinatorial Approach to Identify Anticoagulant Heparan Sulfate Structures
    • DOI 10.1016/j.chembiol.2007.07.015, PII S1074552107002840
    • Chen J, Jones CL, Liu J. 2007. Using an enzymatic combinatorial approach to identify anticoagulant heparan sulfate structures. Chem Biol. 14:986-993. (Pubitemid 47404901)
    • (2007) Chemistry and Biology , vol.14 , Issue.9 , pp. 986-993
    • Chen, J.1    Jones, C.L.2    Liu, J.3
  • 9
    • 45749107540 scopus 로고    scopus 로고
    • Deciphering the glycosaminoglycan code with the help of microarrays
    • DOI 10.1039/b802217h
    • de Paz JL, Seeberger PH. 2008. Deciphering the glycosaminoglycan code with the help of microarrays. Mol Biosyst. 4:707-711. (Pubitemid 351871754)
    • (2008) Molecular BioSystems , vol.4 , Issue.7 , pp. 707-711
    • De Paz, J.L.1    Seeberger, P.H.2
  • 10
    • 29044433102 scopus 로고    scopus 로고
    • Characterization of the N-deacetylase domain from the heparan sulfate N-deacetylase/N-sulfotransferase 2
    • DOI 10.1016/j.bbrc.2005.11.142, PII S0006291X05026859
    • Duncan MB, Liu M, Fox C, Liu J. 2006. Characterization of the N-deacetylase domain from the heparan sulfate N-deacetylase/N-sulfotransferase 2. Biochem Biophys Res Commun. 339:1232-1237. (Pubitemid 41790595)
    • (2006) Biochemical and Biophysical Research Communications , vol.339 , Issue.4 , pp. 1232-1237
    • Duncan, M.B.1    Liu, M.2    Fox, C.3    Liu, J.4
  • 13
    • 58849156045 scopus 로고    scopus 로고
    • Minimum FGF2 binding structural requirements of heparin and heparan sulfate oligosaccharides as determined by NMR spectroscopy
    • Guglieri S, Hricovini M, Raman R, Polito L, Torri G, Casu B, Sasisekharan R, Guerrini M. 2008. Minimum FGF2 binding structural requirements of heparin and heparan sulfate oligosaccharides as determined by NMR spectroscopy. Biochemistry. 47:13862-13869.
    • (2008) Biochemistry , vol.47 , pp. 13862-13869
    • Guglieri, S.1    Hricovini, M.2    Raman, R.3    Polito, L.4    Torri, G.5    Casu, B.6    Sasisekharan, R.7    Guerrini, M.8
  • 14
    • 33846184726 scopus 로고    scopus 로고
    • Highly efficient syntheses of hyaluronic acid oligosaccharides
    • DOI 10.1002/chem.200601090
    • Huang L, Huang X. 2007. Highly efficient synthesis of hyaluronic acid oligosaccharides. Chem Eur J. 13:529-540. (Pubitemid 46104700)
    • (2007) Chemistry - A European Journal , vol.13 , Issue.2 , pp. 529-540
    • Huang, L.1    Huang, X.2
  • 17
    • 33746614761 scopus 로고    scopus 로고
    • Interactions between heparan sulfate and proteins: The concept of specificity
    • DOI 10.1083/jcb.200604035
    • Kreuger J, Spillmann D, Li J-p, Lindahl U. 2006. Interactions between heparan sulfate and proteins: The concept of specificity. J Cell Biol. 174:323-327. (Pubitemid 44156762)
    • (2006) Journal of Cell Biology , vol.174 , Issue.3 , pp. 323-327
    • Kreuger, J.1    Spillmann, D.2    Li, J.-P.3    Lindahl, U.4
  • 18
    • 41449101025 scopus 로고    scopus 로고
    • Disaccharide structure code for the easy representation of constituent oligosaccharides from glycosaminoglycans
    • DOI 10.1038/nmeth0408-291, PII NMETH0408-291
    • Lawrence R, Lu H, Rosenberg R, Esko JD, Zhang L. 2008. Disaccharide structure code for the easy representation of constituent oligosaccharides from glycosaminoglycans. Nat Methods. 5:291-292. (Pubitemid 351455150)
    • (2008) Nature Methods , vol.5 , Issue.4 , pp. 291-292
    • Lawrence, R.1    Lu, H.2    Rosenberg, R.D.3    Esko, J.D.4    Zhang, L.5
  • 19
    • 0025862954 scopus 로고
    • Analysis of affinity and structural selectivity in the binding of proteins to glycosaminoglycans: Development of a sensitive electrophoretic approach
    • Lee MK, Lander AD. 1991. Analysis affinity and structural selectivity in the binding of proteins to glycosaminoglycans: Development of a sensitive electrophoretic approach. Proc Natl Acad Sci USA. 88: 2768-2772. (Pubitemid 21916500)
    • (1991) Proceedings of the National Academy of Sciences of the United States of America , vol.88 , Issue.7 , pp. 2768-2772
    • Lee, M.K.1    Lander, A.D.2
  • 22
    • 0033582432 scopus 로고    scopus 로고
    • Expression of heparan sulfate D-glucosaminyl 3-O-sulfotransferase isoforms reveals novel substrate specificities
    • Liu J, Shworak NW, Sinaÿ P, Schwartz JJ, Zhang L, Fritze LMS, Rosenberg RD. 1999. Expression of heparan sulfate D-glucosaminyl 3-O-sulfotransferase isoforms reveals novel substrate specificities. J Biol Chem. 274:5185-5192.
    • (1999) J Biol Chem , vol.274 , pp. 5185-5192
    • Liu, J.1    Shworak, N.W.2    Sinaÿ, P.3    Schwartz, J.J.4    Zhang, L.5    Lms, F.6    Rosenberg, R.D.7
  • 24
    • 0027448951 scopus 로고
    • Minimal sequence in heparin/heparan sulfate required for binding of basic fibroblast growth factor
    • Maccarana M, Casu B, Lindahl U. 1993. Minimal sequence in heparin/heparan sulfate required for binding of basic fibroblast growth factor. J Biol Chem. 268:23898-23905. (Pubitemid 23335364)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.32 , pp. 23898-23905
    • Maccarana, M.1    Casu, B.2    Lindahl, U.3
  • 26
    • 65349085618 scopus 로고    scopus 로고
    • Designing of biologically active heparan sulfate and heparin using an enzyme-based approach
    • Peterson SP, Frick A, Liu J. 2009. Designing of biologically active heparan sulfate and heparin using an enzyme-based approach. Nat Prod Rep. 26:61-627.
    • (2009) Nat Prod Rep , vol.26 , pp. 61-627
    • Peterson, S.P.1    Frick, A.2    Liu, J.3
  • 27
    • 4544280219 scopus 로고    scopus 로고
    • A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next?
    • DOI 10.1002/anie.200300640
    • Petitou M, van Boeckel CAA. 2004. A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next? Angew Chem Int Ed. 43:3118-3133. (Pubitemid 39257600)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.24 , pp. 3118-3133
    • Petitou, M.1    Van Boeckel, C.A.A.2
  • 29
    • 79957609017 scopus 로고    scopus 로고
    • The dominating role of N-deacetylase/N-sulfotransferase 1 in forming domain structures in heparan sulfate
    • Sheng Z, Liu R, Xu Y, Liu J. 2011. The dominating role of N-deacetylase/N-sulfotransferase 1 in forming domain structures in heparan sulfate. J Biol Chem. 286:19768-19776.
    • (2011) J Biol Chem , vol.286 , pp. 19768-19776
    • Sheng, Z.1    Liu, R.2    Xu, Y.3    Liu, J.4
  • 30
    • 6444222045 scopus 로고    scopus 로고
    • Glycomics: A pathway to a class of new and improved therapeutics
    • DOI 10.1038/nrd1521
    • Shriver Z, Raguram S, Sasisekharan R. 2004. Glycomics: A pathway to a class of new and improved therapeutics. Nat Rev Drug Discov. 3:863-873. (Pubitemid 39405947)
    • (2004) Nature Reviews Drug Discovery , vol.3 , Issue.10 , pp. 863-873
    • Shriver, Z.1    Raguram, S.2    Sasisekharan, R.3
  • 33
    • 77954853474 scopus 로고    scopus 로고
    • Preactivation-based one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions
    • Wang Z, Xu Y, Yang B, Tiruchinapally G, Sun B, Liu R, Dulaney S, Liu J, Huang X. 2010. Preactivation-based one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions. Chem Eur J. 16:8365-8375.
    • (2010) Chem Eur J , vol.16 , pp. 8365-8375
    • Wang, Z.1    Xu, Y.2    Yang, B.3    Tiruchinapally, G.4    Sun, B.5    Liu, R.6    Dulaney, S.7    Liu, J.8    Huang, X.9
  • 34
    • 79956161618 scopus 로고    scopus 로고
    • A comprehensive compositional analysis of heparin/heparan sulfate-derived disac-charides from human serum
    • Wei W, Ninonuevo MR, Sharma A, Dana-Leon LM, Leary JA. 2011. A comprehensive compositional analysis of heparin/heparan sulfate-derived disac-charides from human serum. Anal Chem. 83:3703-3708.
    • (2011) Anal Chem , vol.83 , pp. 3703-3708
    • Wei, W.1    Ninonuevo, M.R.2    Sharma, A.3    Dana-Leon, L.M.4    Leary, J.A.5
  • 35
    • 0037020248 scopus 로고    scopus 로고
    • Heparan sulfate 3-O-sulfotransferase isoform 5 generates both an antithrombin-binding site and an entry receptor for herpes simplex virus, type 1
    • Xia G, Chen J, Tiwari V, Ju W, Li J-P, Malmström A, Shukla D, Liu J. 2002. Heparan sulfate 3-O-sulfotransferase isoform 5 generates both an antithrombin-binding site and an entry receptor for herpes simplex virus, type 1. J Biol Chem. 277:37912-37919.
    • (2002) J Biol Chem , vol.277 , pp. 37912-37919
    • Xia, G.1    Chen, J.2    Tiwari, V.3    Ju, W.4    Li, J.-P.5    Malmström, A.6    Shukla, D.7    Liu, J.8
  • 37
    • 39349108530 scopus 로고    scopus 로고
    • Engineering sulfotransferases to modify heparan sulfate
    • DOI 10.1038/nchembio.66, PII NCHEMBIO66
    • Xu D, Moon A, Song D, Pedersen LC, Liu J. 2008. Engineering sulfotrans-ferases to modify heparan sulfate. Nat Chem Biol. 4:200-202. (Pubitemid 351264127)
    • (2008) Nature Chemical Biology , vol.4 , Issue.3 , pp. 200-202
    • Xu, D.1    Moon, A.F.2    Song, D.3    Pedersen, L.C.4    Liu, J.5
  • 38
    • 0027513987 scopus 로고
    • Structural studies on the bacterial lyase-resistant tetrasaccharides derived from the antithrombin III-binding site of porcine intestinal heparin
    • Yamada S, Yoshida K, Sugiura M, Sugahara K, Khoo KH, Morris HR, Dell A. 1993. Structural studies on the bacterial lyase-resistant tetrasaccharides derived from the antithrombin III-binding site of porcine intestinal heparin. J Biol Chem. 268:4780-4787. (Pubitemid 23081594)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.7 , pp. 4780-4787
    • Yamada, S.1    Yoshida, K.2    Sugiura, M.3    Sugahara, K.4    Khoo, K.-H.5    Morris, H.R.6    Dell, A.7
  • 39
    • 0035863643 scopus 로고    scopus 로고
    • Compositional analysis of glycosaminoglycans by electrospray mass spectrometry
    • DOI 10.1021/ac000777a
    • Zaia J, Costello CE. 2001. Compositional analysis of glycosaminoglycans by electrospray mass spectrometry. Anal Chem. 73:233-239. (Pubitemid 32061834)
    • (2001) Analytical Chemistry , vol.73 , Issue.2 , pp. 233-239
    • Zaia, J.1    Costello, C.E.2
  • 41
    • 0033605256 scopus 로고    scopus 로고
    • Anticoagulant heparan sulfate precursor structures in F9 embryonal carcinoma cells
    • DOI 10.1074/jbc.274.9.5681
    • Zhang L, Yoshida K, Liu J, Rosenberg RD. 1999. Anticoagulant heparan sulfate precursor structures in F9 embryonic carcinoma cells. J Biol Chem. 274:5681-5691. (Pubitemid 29109221)
    • (1999) Journal of Biological Chemistry , vol.274 , Issue.9 , pp. 5681-5691
    • Zhang, L.1    Yoshida, K.2    Liu, J.3    Rosenberg, R.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.