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Volumn 4, Issue 5, 1994, Pages 710-718

Recent developments in glycopeptide and oligosaccharide synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE LINKED OLIGOSACCHARIDE; CARBOHYDRATE; ENZYME; GLYCAN; GLYCOPEPTIDE; GLYCOSYLTRANSFERASE; OLIGOSACCHARIDE; PEPTIDE;

EID: 0028032234     PISSN: 0959440X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0959-440X(94)90169-4     Document Type: Article
Times cited : (63)

References (79)
  • 1
    • 0027419618 scopus 로고
    • Synthesis of Branched Poly-N-acetyl-lactosamine Type Pentaantennary Pentacosasaccharide: Glycan Part of a Glycosyl Ceramide from Rabbit Erythrocyte Membrane
    • of special interest, This impressive synthesis of a penta-antennary polylactosamine oligosaccharide in an outstanding demonstration of the size of the complex structures that can be prepared when a convergent-block strategy with the proper design of syntons is used for the assembly.
    • (1993) Tetrahedron Lett , vol.34 , pp. 1061-1064
    • Matsuzaki1    Ito2    Nakahara3    Ogawa4
  • 2
    • 84986646327 scopus 로고
    • Synthesis of the Pentasaccharide l-α-d-Hep-(1→3)-lα-d-Hep-(1→5)-αKdo-(2→6)-β-d-GlcNhm-(1→6)-d-GlcNhm from the Linear Core- and Lipid-A-structure of Lipopolysaccharides
    • [in German]
    • (1993) Liebigs Annalen der Chemie , pp. 531-541
    • Paulsen1    Höffgen2
  • 4
    • 0027940051 scopus 로고
    • Concise Synthesis of the Calicheamicin Oligosaccharide Using the Sulfoxide Glycosylation Method
    • (1994) J Am Chem Soc , vol.116 , pp. 1766-1775
    • Kim1    Augeri2    Yang3    Kahne4
  • 6
    • 0027360551 scopus 로고
    • Synthesis of Oligosaccharides, Glycopeptides, and Glycolipids
    • (1993) Strict Biol , vol.3 , pp. 694-700
    • Halcomb1    Wong2
  • 7
    • 5244279498 scopus 로고
    • Recent Progress in O-Glycosylation Methods and Its Application to Natural Product Synthesis
    • (1993) Chem Rev , vol.93 , pp. 1503-1531
    • Toshima1    Tatsita2
  • 12
    • 0027086437 scopus 로고
    • Glycosylation Using a One-electron-transfer, Homogeneous Reagent. Application to an Efficient Synthesis of the Trimannosyl Core of N-Glycosylproteins
    • (1992) Carbohydr Res , vol.236 , pp. 73-88
    • Zhang1    Mallet2    Sinaÿ3
  • 13
    • 33751386390 scopus 로고
    • Novel Glycosidation Methodology The Use of Phenyl Selenoglycosides as Glycosyl Donors and Acceptors in Oligosaccharide Synthesis
    • (1993) The Journal of Organic Chemistry , vol.58 , pp. 3269-3276
    • Metha1    Pinto2
  • 14
    • 0027538622 scopus 로고
    • A One Step Synthesis of the Ciclamycin Trisaccharide
    • of outstanding interest, In this work differential activation of two 2-deoxy glycosyl donors as substituted anomeric phenyl sulfoxides and silyl masking of one of two hydroxy acceptors has allowed, for the first time, a completely selective one-pot synthesis of a trisaccharide with two different donors. It remains to be seen whether the approach can find general application in oligosaccharide synthesis.
    • (1993) J Am Chem Soc , vol.115 , pp. 1580-1581
    • Raghavan1    Kahne2
  • 18
    • 0027158301 scopus 로고
    • A New Multi-enzyme System for a One-pot Synthesis of Sialyl Oligosaccharides: Combined Use of β-Galactosidase and α(2,6)-sialyltransferase Coupled with Regeneration in situ of CMP-sialic Acid
    • (1993) Tetrahedron Lett , vol.34 , pp. 3091-3094
    • Herrmann1    Ichikawa2    Wandrey3    Gaeta4    Paulsen5    Wong6
  • 20
    • 0027591808 scopus 로고
    • A Strategy for the Solid-phase Synthesis of Oligosaccharides
    • of special interest, The first successful solid-phase synthesis of a more complex oligosaccharide was achieved by Danishefsky et al.. This elegant work uses the anomeric oxidation of glycals into oxiranes, which are activated on the solid phase for stereoselective glycosylation reactions. A silyl linkage to the non-reducing end allows selective release of the oligosaccharide at the end of the synthesis. The complete stereoselectivity of the glycosylation is still a matter of debate [21].
    • (1993) Science , vol.260 , pp. 1307-1309
    • Danishefsky1    McClure2    Randolph3    Ruggeri4
  • 22
    • 0001357306 scopus 로고
    • Polymer-supported Solution Synthesis of a Heptaglucoside Having Phytoalexin Elicitor Activity
    • of special interest, In this work a heptasaccharide was synthesized without purification during intermediate steps by using a PEG derivatization, which simultaneously allowed glycosylation in solution and quantitative precipitation of reaction products. Only highly selective β-glycosylation reactions were used.
    • (1993) Recl Trav Chim Pays-Bas , vol.112 , pp. 464-466
    • Verduyn1    van der Klein2    Douwes3    van der Marel4    Van Boom5
  • 23
    • 0027593330 scopus 로고
    • x-containing Hexasaccharide Found on 0-linked Glycoproteins
    • of outstanding interest, This incredibly fast synthesis of a sialyl Lewis-X containing hexasaccharide uses a lipophilic spacer for the solid phase extraction of glycosylation products in combination with virtually quantitative glycosylations using glycosyltransferases. This method will have considerable potential as the transferases become more available.
    • (1993) Carbohydr Res , vol.244 , pp. 149-159
    • Oehrlein1    Hindsgaul2    Palcic3
  • 24
    • 0000312537 scopus 로고
    • Ligand Recognition by E-Selectin Analysis of Conformation and Activity of Synthetic Monomeric and Bivalent Sialyl Lewis-X Analogs
    • (1993) J Am Chem Soc , vol.115 , pp. 7549-7550
    • Defrees1    Gaeta2    Lin3    Ichikawa4    Wong5
  • 27
    • 0001568673 scopus 로고
    • Intramolecular Glycosidation Stereocontrolled Synthesis of α-Glycosides from a 2-O-Alkoxysilyl Thioglycoside
    • (1993) Acta Chemica Scandinavica , vol.47 , pp. 829-834
    • Bols1
  • 28
    • 0027437186 scopus 로고
    • Efficient Stereocontrolled Glycosidation of Secondary Sugar Hydroxyls by Silicon Tethered Intramolecular Glycosidation
    • (1993) Tetrahedron , vol.49 , pp. 10049-10060
    • Bols1
  • 31
    • 0027442501 scopus 로고
    • Piperidine Is Preferable to Morpholine for Fmoc Cleavage in Solid Phase Synthesis of O-Linked Glycopeptides
    • (1993) Tetrahedron Lett , vol.34 , pp. 6135-6138
    • Kihlberg1    Vuljanic2
  • 34
  • 35
    • 0028544958 scopus 로고
    • Silyl Protection in the Solid-phase Synthesis of N-Linked Glycopeptides. Preparation of Glycosylated Fluorogenic Substrates for Subtilisins
    • of special interest, in press, In this work a method was developed for an efficient two-step preparation affording completely protected large building blocks for N-linked glycopeptide assembly. By synthesis of glycosylated internally quenched fluorogenic peptide substrates, the authors provide the first evidence that the glycosylation may confer specificity on the proteolytic cleavage of glycosylated peptides and proteins.
    • (1994) Bioorg Med Chem Lett
    • Christiansen-Brams1    Jansson2    Meldal3    Breddam4    Bock5
  • 38
    • 0027222172 scopus 로고
    • Synthetic Glycosylation of Peptides Using Unprotected Saccharide Glycosylamines
    • of special interest, Both this and [38•] describe a convergent approach to the synthesis of N-linked glycopeptides which allow even large complex structures isolated from nature to be incorporated into glycopeptides on the solid phase by selective activation of an aspartic acid residue. Partial suppression of side reactions such as aspartimide formation was achieved.
    • (1993) Glycoconjugate J , vol.10 , pp. 227-234
    • Wong1    Guile2    Rademacher3    Dwek4
  • 39
    • 0001270462 scopus 로고
    • A Practical, Convergent Method for Glycopeptide Synthesis
    • of special interest, Both this and [38•] describe a convergent approach to the synthesis of N-linked glycopeptides which allow even large complex structures isolated from nature to be incorporated into glycopeptides on the solid phase by selective activation of an aspartic acid residue. Partial suppression of side reactions such as aspartimide formation was achieved.
    • (1993) J Am Chem Soc , vol.115 , pp. 10531-10537
    • Cohen-Anisfeld1    Lansbury2
  • 41
    • 0027607433 scopus 로고
    • Total Synthesis of the Carbohydrate-protein Linkage Region Common to Several Mammalian Proteoglycans
    • of special interest, A tetrasaccharide trichloroacetimidate from the proteoglycan core was prepared as a shelf-stable building block. It was used for glycosylation of a dipeptide and the resulting glycopeptide was used in fragment condensations to construct impressive model compounds of proteoglycans.
    • (1993) Carbohydr Res , vol.244 , pp. 295-313
    • Rio1    Beau2    Jacquinet3
  • 42
    • 84988080209 scopus 로고
    • A New strategy for Fast Solid-Phase Synthesis of O-Glycopeptiden via 2-Azido-glycopeptide
    • of special interest, [in German], A much improved and more direct procedure for the preparation of mucin glycopeptides was described. The 2-azido-2-deoxygalactose obtained by azidonitration was directly incorporated into an activated amino acid to form a building block for solid-phase synthesis. The azide was quantitatively converted into the desired acetamide after peptide assembly.
    • (1994) Liebigs Annalen der Chemie , pp. 369-379
    • Paulsen1    Bielfeldt2    Peters3    Meldal4    Bock5
  • 51
    • 37049066793 scopus 로고
    • Synthesis of Glycosylated Peptide Templates Containing 6′-O-Phosphorylated Mannose Disaccharides and Their Binding to the Mannose-6-phosphate Receptor
    • of outstanding interest, This work defines the minimum requirement for the successful synthesis of high-affinity glycopeptide ligands for receptors in which several domains are involved in the interaction with a complex carbohydrate ligand. The authors demonstrated that the mannose 6-phosphate receptor interacts directly with two Man6P-(1→2)-Man disaccharides and the rest of the oligosaccharide can be replaced with peptide templates. The approach may have considerable potential for defining the structure, function and distribution of mammal lectins.
    • (1994) Journal of the Chemical Society, Perkin Transactions 1 , pp. 1299-1316
    • Christensen1    Meldal2    Bock3    Cordes4    Mouritsen5    Elsner6
  • 55
    • 0028762251 scopus 로고
    • Chemical and Enzymatic Synthesis of Multivalent Sialoglycopeptides
    • of special interest, The use of enzymes to glycosylate several identical glycosyl acceptors has allowed the efficient synthesis of a number of multivalent sialoglycopeptides as possible inhibitors of the influenza virus. This approach is a general method for obtaining glycopeptides containing several identical complex oligosaccharides. Unfortunately, the prepared compounds did not show the expected activity.
    • (1994) Carbohydr Res , vol.251 , pp. 285-301
    • Unverzagt1    Kelm2    Paulson3
  • 57
    • 0027951227 scopus 로고
    • Solid-phase Chemical-enzymatic Synthesis of Glycopeptides and Oligosaccharides
    • of outstanding interest, The first successful solid-phase enzymatic oligosaccharide synthesis was reported. Two enzymatic glycosylations of a small glycopeptide were performed on a silica-gel surface, and in this way the previous problems of inaccessibility of the interior of polystyrene resins were overcome to yield 55–65% in enzyme-catalyzed reactions.
    • (1994) J Am Chem Soc , vol.116 , pp. 1135-1136
    • Schuster1    Wang2    Paulson3    Wong4
  • 58
    • 0029171257 scopus 로고
    • Synthesis Characterization and Biocompatibility of PEGA Resins
    • of special interest, New peptide-synthesis resins with improved performance are a prerequisite for successful synthesis of peptides and glycopeptides. Particularly biocompatible resins are required for the successful application of resins to portion-mixing libraries for biological studies. This paper describe a step forward in this direction.
    • (1994) Journal of Peptide Science , vol.1 , pp. 31-44
    • Auzanneau1    Meldal2    Bock3
  • 60
    • 37049067264 scopus 로고
    • A PEGA Resin for Use in Solid Phase Chemical/Enzymatic Synthesis of Glycopeptides
    • of outstanding interest, The design of a new type of highly swelling and flexible PEG-based polymer in the form of a beaded resin has allowed quantitative solid phase glycosylatioin of a glycopeptide using glycosyltransferase. The resin, which is a versatile alternative to the silica gel approach mentioned above, allows full access of transferases of up to 5O kDa into the interior and may be modified to accommodate even larger proteins.
    • (1994) Journal of the Chemical Society, Chemical Communications , pp. 1849-1850
    • Meldal1    Auzanneau2    Hindsgaul3    Palcic4
  • 62
    • 0028041060 scopus 로고
    • A General Approach to the Synthesis of O- and N-Linked Glycopeptides
    • (1994) Glycoconjugate J , vol.11 , pp. 59-63
    • Meldal1    Bock2
  • 63
  • 68
    • 0025425218 scopus 로고
    • Synthesis of a Branched Glycopeptide Derivative Containing Terminal d-Mannose 6-Phosphate Residues
    • (1990) Carbohydr Res , vol.198 , pp. 235-246
    • Ichikawa1    Lee2
  • 70
    • 0027857964 scopus 로고
    • De Novo Design and Synthesis of Somatostatin Non-peptide Peptidomimetics Utilizing β-d-Glucose as a Novel Scaffolding
    • of outstanding interest, This outstanding research describes the synthesis of a non-peptide peptidomimetic in which a glucopyranose scaffold mimics the cyclic part of the peptide backbone of somatostatin. The interacting side chains of the peptide are simulated by the attachment of similar functional groups to the hydroxy groups of the glucopyranose. This approach may well be a general way of mimicking small-peptide hormones.
    • (1993) J Am Chem Soc , vol.115 , pp. 12550-12568
    • Hirschmann1    Nicolaou2    Pietranico3    Leahy4    Salvino5    Arison6    Cichy7    Spoors8    Shakespeare9    Sprengeler10
  • 76
    • 0027643018 scopus 로고
    • Solid-phase Synthesis and Conformational Studies of Glycosylated Derivatives of Helper-T-cell immunogenic Peptides from Hen-egg Lysozyme
    • (1993) Carbohydr Res , vol.246 , pp. 89-103
    • Elofsson1    Roy2    Walse3    Kihlberg4
  • 79
    • 0000134730 scopus 로고
    • Synthesis of Glycosyl-enkephalin Analogues which Rapidly Cross the Blood-Brain Barrier to Produce Analgesia in Mice An Entirely New Class of ‘Designer Drugs’
    • of special interest, Enkephalin glycopeptides were synthesized and found to rapidly cross the blood-brain barrier. This new principle of glycosylation of peptides in order to introduce glycans as markers for recognition and active transport across membranes may have great potential for drug delivery. Furthermore, the glycosylation can increase the lifetime of the active peptide by providing protection against proteolylic degradation.
    • (1994) Glycoconjugate Journal , vol.10 , pp. 261
    • Poll1    Porecca2    Szabo3    Hruby4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.