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Volumn 3, Issue 3, 1999, Pages 291-298

Combinatorial synthesis of carbohydrates

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOSACCHARIDE; SOMATOSTATIN DERIVATIVE; SUGAR;

EID: 0033152001     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(99)80045-3     Document Type: Article
Times cited : (101)

References (45)
  • 1
    • 0027318961 scopus 로고
    • Biological roles of oligosaccharides: All of the theories are correct
    • Varki A: Biological roles of oligosaccharides: All of the theories are correct. Glycobiology 1993, 3:97-130.
    • (1993) Glycobiology , vol.3 , pp. 97-130
    • Varki, A.1
  • 2
    • 0031152054 scopus 로고    scopus 로고
    • Combinatorial approaches to carbohydrates
    • Kahne D: Combinatorial approaches to carbohydrates. Curr Opin Chem Biol 1997, 1:130-135.
    • (1997) Curr Opin Chem Biol , vol.1 , pp. 130-135
    • Kahne, D.1
  • 3
    • 0001300898 scopus 로고    scopus 로고
    • Combinatorial carbohydrate chemistry
    • Wang ZG, Hindsgaul O: Combinatorial carbohydrate chemistry. Glycoimmunology 1998, 2:219-236.
    • (1998) Glycoimmunology , vol.2 , pp. 219-236
    • Wang, Z.G.1    Hindsgaul, O.2
  • 4
    • 0031994805 scopus 로고    scopus 로고
    • Carbohydrate-based combinatorial libraries
    • Sofia MJ: Carbohydrate-based combinatorial libraries. Mol Divers 1998, 3:75-94. This is an excellent review article on carbohydrate-based libraries, with special emphasis on glycopeptide libraries. There is extensive literature coverage prior to 1998.
    • (1998) Mol Divers , vol.3 , pp. 75-94
    • Sofia, M.J.1
  • 5
    • 0028243847 scopus 로고
    • Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries
    • Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM: Application of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J Med Chem 1994, 37:1233-1251.
    • (1994) J Med Chem , vol.37 , pp. 1233-1251
    • Gallop, M.A.1    Barrett, R.W.2    Dower, W.J.3    Fodor, S.P.A.4    Gordon, E.M.5
  • 6
    • 0028318863 scopus 로고
    • Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies and future directions
    • Gallop MA, Barrett RW, Dower WJ, Fodor SPA, Gordon EM: Application of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies and future directions. J Med Chem 1994, 37:1385-1401.
    • (1994) J Med Chem , vol.37 , pp. 1385-1401
    • Gallop, M.A.1    Barrett, R.W.2    Dower, W.J.3    Fodor, S.P.A.4    Gordon, E.M.5
  • 7
    • 0033521531 scopus 로고    scopus 로고
    • Micro-scale frontal affinity chromatography with mass spectrometric detection: A new method for the screening of compound libraries
    • Schriemer DC, Bundle DR, Li L, Hindsgaul O: Micro-scale frontal affinity chromatography with mass spectrometric detection: A new method for the screening of compound libraries. Angew Chem Int Ed Engl 1998, 37:3383-3387. This new screening method allows the identification of the structure of individual 'hits' in a mixture of compounds and can thus eliminate 'false positives' that arise from reaction byproducts or impurities. Furthermore, binding constants can be determined for individual compounds present in a mixture.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 3383-3387
    • Schriemer, D.C.1    Bundle, D.R.2    Li, L.3    Hindsgaul, O.4
  • 8
    • 0030599268 scopus 로고    scopus 로고
    • Polymer-supported synthesis of oligosaccharides: Using dibutylboron triflate to promote glycosylations with glycosyl trichloroacetimidates
    • Wang ZG, Douglas S, Krepinsky JJ: Polymer-supported synthesis of oligosaccharides: Using dibutylboron triflate to promote glycosylations with glycosyl trichloroacetimidates. Tetrahedron Lett 1996, 37:6985-6988.
    • (1996) Tetrahedron Lett , vol.37 , pp. 6985-6988
    • Wang, Z.G.1    Douglas, S.2    Krepinsky, J.J.3
  • 11
    • 0029895067 scopus 로고    scopus 로고
    • Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine
    • Ding Y, Labbe J, Kanie O, Hindsgaul O: Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine. Bioorg Biomed Chem 1996, 4:683-692.
    • (1996) Bioorg Biomed Chem , vol.4 , pp. 683-692
    • Ding, Y.1    Labbe, J.2    Kanie, O.3    Hindsgaul, O.4
  • 12
    • 0032499152 scopus 로고    scopus 로고
    • Combinatorial synthesis of oligosaccharide library of 2,6-dideoxysugars
    • Izumi M, Ichikawa Y: Combinatorial synthesis of oligosaccharide library of 2,6-dideoxysugars. Tetrahedron Lett 1998, 39:2079-2082.
    • (1998) Tetrahedron Lett , vol.39 , pp. 2079-2082
    • Izumi, M.1    Ichikawa, Y.2
  • 13
    • 0030484272 scopus 로고    scopus 로고
    • Vinyl glycosides in oligosaccharide synthesis: A strategy for the preparation of trisaccharide libraries based on latent-active glycosylation
    • Boons GJ, Heskamp B, Hout F: Vinyl glycosides in oligosaccharide synthesis: A strategy for the preparation of trisaccharide libraries based on latent-active glycosylation. Angew Chem Int Ed Engl 1996, 35:2845-2847.
    • (1996) Angew Chem Int Ed Engl , vol.35 , pp. 2845-2847
    • Boons, G.J.1    Heskamp, B.2    Hout, F.3
  • 15
    • 0032558124 scopus 로고    scopus 로고
    • Assembly of oligosaccharide libraries with a designed building block and an efficient orthogonal protection-deprotection strategy
    • Wong C-H, Ye X-S, Zhang Z: Assembly of oligosaccharide libraries with a designed building block and an efficient orthogonal protection-deprotection strategy. J Am Chem Soc 1998, 120:7137-7138. Four orthogonal protecting groups on a central building block combined with high yielding glycosylation reactions allow the combinatorial solution-phase synthesis of a highly branched oligosaccharide library containing tri-, tetra-and pentasaccharides.
    • (1998) J Am Chem Soc , vol.120 , pp. 7137-7138
    • Wong, C.-H.1    Ye, X.-S.2    Zhang, Z.3
  • 16
    • 0032479729 scopus 로고    scopus 로고
    • A two-directional approach for the solid phase synthesis of trisaccharide libraries
    • Zhu T, Boons G-J: A two-directional approach for the solid phase synthesis of trisaccharide libraries. Angew Chem Int Ed Engl 1998, 37:1898-1900. Two consecutive glycosylation reactions using thioglycoside donors allow the synthesis of a small trisaccharide library. The initial immobilized donor becomes an immobilized acceptor during the synthesis.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 1898-1900
    • Zhu, T.1    Boons, G.-J.2
  • 17
    • 0032547050 scopus 로고    scopus 로고
    • Solid phase synthesis of oligosaccharides: Construction of a dodecasaccharide
    • Nicolaou KC, Watanabe N, Li J, Pastor J, Winssinger N: Solid phase synthesis of oligosaccharides: Construction of a dodecasaccharide. Angew Chem Int Ed Engl 1998, 37:1559-1561. This paper describes the synthesis of a dodecasaccharide via convergent block synthesis on the solid phase. A novel photocleavable aglycon linker allows the resin cleavage and activation to a new thioglycoside donor to proceed in one step, making this a very efficient approach for the synthesis of large oligosaccharides.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 1559-1561
    • Nicolaou, K.C.1    Watanabe, N.2    Li, J.3    Pastor, J.4    Winssinger, N.5
  • 18
    • 0001207175 scopus 로고    scopus 로고
    • Solid support oligosaccharide synthesis: Construction of β-linked oligosaccharides by coupling of glycal derived thioethyl glycosyl donors
    • Zheng C, Seeberger PH, Danishefsky SJ: Solid support oligosaccharide synthesis: Construction of β-linked oligosaccharides by coupling of glycal derived thioethyl glycosyl donors. J Org Chem 1998, 63:1126-1130. An efficient conversion of immobilized glucal into 1-thioethyl-2-O-pivaloxy donors permits the solid-phase synthesis of β-(1,4)-linked triglucosides and tetraglucosides.
    • (1998) J Org Chem , vol.63 , pp. 1126-1130
    • Zheng, C.1    Seeberger, P.H.2    Danishefsky, S.J.3
  • 19
    • 0031924817 scopus 로고    scopus 로고
    • b blood group determinant
    • b blood group determinant. Angew Chem Int Ed Engl 1998, 37:786-789. Polymer-bound glycals can be converted into ethylsulfanyl-2-amidoglucosyl donors, thereby permitting the solid-phase synthesis of oligosaccharides incorporating a 2-deoxy-2-acetylamido-glucose unit.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 786-789
    • Zheng, C.1    Seeberger, P.H.2    Danishefsky, S.J.3
  • 20
    • 0002295513 scopus 로고    scopus 로고
    • Oligosaccharide synthesis on controlled-pore glass as solid phase material
    • Heckel A, Mross E, Jung KH, Rademann J, Schmidt R: Oligosaccharide synthesis on controlled-pore glass as solid phase material. Synlett 1998:171-173.
    • (1998) Synlett , pp. 171-173
    • Heckel, A.1    Mross, E.2    Jung, K.H.3    Rademann, J.4    Schmidt, R.5
  • 21
    • 0000532889 scopus 로고    scopus 로고
    • Efficient synthesis of diverse monosaccharide derivatives in the solid phase
    • Kobayashi S, Wakabayashi T, Yasuda M: Efficient synthesis of diverse monosaccharide derivatives in the solid phase. J Org Chem 1998, 63:4868-4869.
    • (1998) J Org Chem , vol.63 , pp. 4868-4869
    • Kobayashi, S.1    Wakabayashi, T.2    Yasuda, M.3
  • 22
    • 0027951227 scopus 로고
    • Solid phase chemical-enzymatic synthesis of glycopeptides and oligosaccharides
    • Schuster M, Wang P, Paulson JC, Wong C-H: Solid phase chemical-enzymatic synthesis of glycopeptides and oligosaccharides. J Am Chem Soc 1994, 116:1135-1136.
    • (1994) J Am Chem Soc , vol.116 , pp. 1135-1136
    • Schuster, M.1    Wang, P.2    Paulson, J.C.3    Wong, C.-H.4
  • 23
    • 0029801847 scopus 로고    scopus 로고
    • Generation of C-glycoside peptide ligands for cell surface carbohydrate receptors using a four component condensation on solid support
    • Sutherlin DP, Stark TM, Hughes R, Armstrong RW: Generation of C-glycoside peptide ligands for cell surface carbohydrate receptors using a four component condensation on solid support. J Org Chem 1996, 61:8350-8354.
    • (1996) J Org Chem , vol.61 , pp. 8350-8354
    • Sutherlin, D.P.1    Stark, T.M.2    Hughes, R.3    Armstrong, R.W.4
  • 24
    • 0029905917 scopus 로고    scopus 로고
    • Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev response element
    • Park WKC, Auer M, Jaksche H, Wong C-H: Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev response element. J Am Chem Soc 1996, 118:10150-10155.
    • (1996) J Am Chem Soc , vol.118 , pp. 10150-10155
    • Park, W.K.C.1    Auer, M.2    Jaksche, H.3    Wong, C.-H.4
  • 26
    • 0032168143 scopus 로고    scopus 로고
    • Solid phase extraction on C18 silica as a purification strategy in the solution synthesis of a 1-thio-β-D-galactopyranoside library
    • Nilsson UJ, Fournier EJ-L, Hindsgaul O: Solid phase extraction on C18 silica as a purification strategy in the solution synthesis of a 1-thio-β-D-galactopyranoside library. Bioorg Med Chem 1998, 6:1563-1575. Solution-phase combinatorial synthesis with hydrophobically tagged sugar monomers allows fast and easy purification of products via simple solid-phase extraction and conventional reaction monitoring.
    • (1998) Bioorg Med Chem , vol.6 , pp. 1563-1575
    • Nilsson, U.J.1    Fournier, E.J.-L.2    Hindsgaul, O.3
  • 27
    • 0020211577 scopus 로고
    • From isocyanides via four-component condensations to antibiotic synthesis
    • Ugi I: From isocyanides via four-component condensations to antibiotic synthesis. Angew Chem Int Ed Engl 1982, 21:810-819.
    • (1982) Angew Chem Int Ed Engl , vol.21 , pp. 810-819
    • Ugi, I.1
  • 28
    • 0033521568 scopus 로고    scopus 로고
    • An acess to glyconjugate libraries through multicomponent reactions
    • Lockhoff O: An acess to glyconjugate libraries through multicomponent reactions. Angew Chem Int Ed Engl 1998, 37:3436-3439. Glucosyl-based amines, aldehydes, acids and isocyantes were investigated for use in the Ugi and Passerini reactions. Under certain conditions, all four glucose-based components condensed with each other.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 3436-3439
    • Lockhoff, O.1
  • 29
    • 0032569212 scopus 로고    scopus 로고
    • A library approach to the discovery of small molecules that recognize RNA: Use of a 1,3-hydroxyamine motif as core
    • Wong C-H, Hendrix M, Manning DD, Rosenbohm C, Greenberg WA: A library approach to the discovery of small molecules that recognize RNA: Use of a 1,3-hydroxyamine motif as core. J Am Chem Soc 1998, 120:8319-8327. The binding affinity of a small sugar-based 1,3-hydroxyamine library binding to model RNA spans about two orders of magnitude but shows no sequence specificity. The results suggest that larger and more diversified libraries may eventually provide specific RNA binders.
    • (1998) J Am Chem Soc , vol.120 , pp. 8319-8327
    • Wong, C.-H.1    Hendrix, M.2    Manning, D.D.3    Rosenbohm, C.4    Greenberg, W.A.5
  • 30
    • 0030745434 scopus 로고    scopus 로고
    • Hydroxyamines as a new motif for the molecular recognition of phosphodiesters: Implications for aminoglycoside-RNA interactions
    • Hendrix M, Alper PB, Priestly ES, Wong C-H: Hydroxyamines as a new motif for the molecular recognition of phosphodiesters: Implications for aminoglycoside-RNA interactions. Angew Chem Int Ed Engl 1997, 36:95-98.
    • (1997) Angew Chem Int Ed Engl , vol.36 , pp. 95-98
    • Hendrix, M.1    Alper, P.B.2    Priestly, E.S.3    Wong, C.-H.4
  • 32
    • 0029882333 scopus 로고    scopus 로고
    • Glycosamino acids: New building blocks for combinatorial synthesis
    • McDevitt JP, Lansbury PT: Glycosamino acids: New building blocks for combinatorial synthesis. J Am Chem Soc 1996, 118:3818-3828.
    • (1996) J Am Chem Soc , vol.118 , pp. 3818-3828
    • McDevitt, J.P.1    Lansbury, P.T.2
  • 33
    • 0000496054 scopus 로고    scopus 로고
    • Solid phase synthesis and secondary structural studies of (1→5) amide-linked sialooligomers
    • Szabo L, Smith BL, McReynolds KD, Parrill AL, Morris ER, Gervay J: Solid phase synthesis and secondary structural studies of (1→5) amide-linked sialooligomers. J Org Chem 1998, 63:1074-1078. This study provides the first evidence that oligomers comprising constrained carbohydrate-derived amino acids form stable secondary structures in water.
    • (1998) J Org Chem , vol.63 , pp. 1074-1078
    • Szabo, L.1    Smith, B.L.2    McReynolds, K.D.3    Parrill, A.L.4    Morris, E.R.5    Gervay, J.6
  • 34
    • 0030817956 scopus 로고    scopus 로고
    • Combinatorial chemistry of piperidine based carbohydrate mimics
    • Byrgesen E, Nielsen J, Willert M, Bols M: Combinatorial chemistry of piperidine based carbohydrate mimics. Tetrahedron Lett 1997, 38:5697-5700.
    • (1997) Tetrahedron Lett , vol.38 , pp. 5697-5700
    • Byrgesen, E.1    Nielsen, J.2    Willert, M.3    Bols, M.4
  • 36
    • 0030569319 scopus 로고    scopus 로고
    • Solid phase synthesis of peptidoglycan monomers for the generation of a combinatorial library
    • Chan TY, Chen A, Allanson N, Chen R, Liu D, Sofia MJ: Solid phase synthesis of peptidoglycan monomers for the generation of a combinatorial library. Tetrahedron Lett 1996, 37:8097-8100.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8097-8100
    • Chan, T.Y.1    Chen, A.2    Allanson, N.3    Chen, R.4    Liu, D.5    Sofia, M.J.6
  • 37
    • 0011217950 scopus 로고    scopus 로고
    • Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries
    • St Hilaire PM, Lowary TL, Meldal M, Bock K: Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries. J Am Chem Soc 1998, 120:13312-13320. A 300,000-member encoded glycopeptide library was synthesized on the solid phase and screened (on-bead) with a fluorescently labeled methyl α-D-mannose binding lectin. Interestingly, the most active compounds were glycopeptides containing only α-D-mannose residues, which displayed up to a 25-fold increase in binding.
    • (1998) J Am Chem Soc , vol.120 , pp. 13312-13320
    • St Hilaire, P.M.1    Lowary, T.L.2    Meldal, M.3    Bock, K.4
  • 39
    • 15444347630 scopus 로고    scopus 로고
    • Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis
    • Hirschmann R, Hynes Jr J, Cichy-Knight MA, van Rijn RD, Sprengeler PA, Spoors PG Shakespeare WC, Pietranico-Cole S, Barbosa J, Liu J et al.: Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis. J Med Chem 1998, 41:1382-1391. This study shows for the first time that subtle modifications on a sugar scaffold can generate various levels of specificity and potency against different receptors and receptor subtypes.
    • (1998) J Med Chem , vol.41 , pp. 1382-1391
    • Hirschmann, R.1    Hynes J., Jr.2    Cichy-Knight, M.A.3    Van Rijn, R.D.4    Sprengeler, P.A.5    Spoors, P.G.6    Shakespeare, W.C.7    Pietranico-Cole, S.8    Barbosa, J.9    Liu, J.10
  • 40
    • 0347190177 scopus 로고    scopus 로고
    • Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids
    • Graf von Roedern E, Lohof E, Hessler G, Hoffmann M, Kessler H: Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids. J Am Chem Soc 1996, 118:10156-10167.
    • (1996) J Am Chem Soc , vol.118 , pp. 10156-10167
    • Graf Von Roedern, E.1    Lohof, E.2    Hessler, G.3    Hoffmann, M.4    Kessler, H.5
  • 42
    • 0032539206 scopus 로고    scopus 로고
    • Folded conformation in peptides containing furanoid sugar amino acids
    • Chakraborty TK, Jayaprakash S, Diwan PV, Nagaraj R, Jampani SRB, Kunwar AC: Folded conformation in peptides containing furanoid sugar amino acids. J Am Chem Soc 1998, 120:12962-12963. Incorporation of furanoid sugar amino acids into enkephalin peptides induces unusual secondary structures. Simple modifications on the sugar-furan scaffold resulted in pronounced biological activity differences.
    • (1998) J Am Chem Soc , vol.120 , pp. 12962-12963
    • Chakraborty, T.K.1    Jayaprakash, S.2    Diwan, P.V.3    Nagaraj, R.4    Jampani, S.R.B.5    Kunwar, A.C.6
  • 43
    • 0000845917 scopus 로고    scopus 로고
    • Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries
    • Sofia MJ, Hunter R, Chan TY, Vaughan A, Dulina R, Wang H, Gange D: Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries. J Org Chem 1998, 63:2802-2803. Incorporation of a carboxylic acid, a free hydroxyl group and a protected amino group into the sugar scaffold permits efficient three-point functionalization of the carbohydrate scaffold. The building block behaves like an amino acid and allows facile access to libraries.
    • (1998) J Org Chem , vol.63 , pp. 2802-2803
    • Sofia, M.J.1    Hunter, R.2    Chan, T.Y.3    Vaughan, A.4    Dulina, R.5    Wang, H.6    Gange, D.7
  • 44
    • 0032476094 scopus 로고    scopus 로고
    • Carbohydrates as multifunctional chiral scaffolds in combinatorial synthesis
    • Wunberg T, Kallus C, Opatz T, Henke S, Schmidt W, Kunz H: Carbohydrates as multifunctional chiral scaffolds in combinatorial synthesis. Angew Chem Int Ed Engl 1998, 37:2503-2505. This paper describes a novel strategy that allows the generation of polyether libraries derived from carbohydrates. These kinds of compounds may find use as nonpeptide peptidomimetics in the future.
    • (1998) Angew Chem Int Ed Engl , vol.37 , pp. 2503-2505
    • Wunberg, T.1    Kallus, C.2    Opatz, T.3    Henke, S.4    Schmidt, W.5    Kunz, H.6
  • 45


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