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Solid-phase synthesis of oligosaccharides and glycoconjugates

Nikolai Konstantinovich Kochetkov 1
Nikolai Konstantinovich Kochetkov
1 N. D. Zelinskii Institute of Organic Chemistry, Moscow
Published 30 November 1999
Communication , Volume 69, Issue 9, 795-820
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Kochetkov N. K. Solid-phase synthesis of oligosaccharides and glycoconjugates // Russian Chemical Reviews. 2000. Vol. 69. No. 9. pp. 795-820.
GOST all authors (up to 50)
Kochetkov N. K. Solid-phase synthesis of oligosaccharides and glycoconjugates // Russian Chemical Reviews. 2000. Vol. 69. No. 9. pp. 795-820.
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RIS
TY - JOUR
DO - 10.1070/RC2000v069n09ABEH000568
UR - https://rcr.colab.ws/publications/10.1070/RC2000v069n09ABEH000568
TI - Solid-phase synthesis of oligosaccharides and glycoconjugates
T2 - Russian Chemical Reviews
AU - Kochetkov, Nikolai Konstantinovich
PY - 2000
DA - 1999/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 795-820
IS - 9
VL - 69
ER -
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@article{2000_Kochetkov,
author = {Nikolai Konstantinovich Kochetkov},
title = {Solid-phase synthesis of oligosaccharides and glycoconjugates},
journal = {Russian Chemical Reviews},
year = {2000},
volume = {69},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2000v069n09ABEH000568},
number = {9},
pages = {795--820},
doi = {10.1070/RC2000v069n09ABEH000568}
}
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Cite this
MLA
Kochetkov, Nikolai Konstantinovich. “Solid-phase synthesis of oligosaccharides and glycoconjugates.” Russian Chemical Reviews, vol. 69, no. 9, Nov. 2000, pp. 795-820. https://rcr.colab.ws/publications/10.1070/RC2000v069n09ABEH000568.
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Abstract

The use of polymeric supports for directed regiospecific assembly of oligosaccharides, glycopeptides and phosphoglycans is considered. In some cases, synthesis of oligosaccharides on supports is more efficient than the corresponding synthesis in solution, although this cannot still compare favourably with the latter. Examples of successful solid-phase syntheses of complex oligosaccharides and glycoconjugates are given. Special emphasis is laid on the choice of optimum supports, linkers and glycosylation methods. The bibliography includes 105 references.

References

1.
Solid Phase Peptide Synthesis. I. The Synthesis of a Tetrapeptide
Merrifield R.B.
Journal of the American Chemical Society , 1963
4.
Solid-phase synthesis of oligosacchapides
Frécget J.M., Schuerch C.
Carbohydrate Research , 1972
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
A General and Highly Efficient Solid Phase Synthesis of Oligosaccharides. Total Synthesis of a Heptasaccharide Phytoalexin Elicitor (HPE)
Nicolaou K.C., Winssinger N., Pastor J., DeRoose F.
Journal of the American Chemical Society , 1997
9.
Solid-Phase Synthesis of 6-Deoxyoligosaccharides
Hunt J.A., Roush W.R.
Journal of the American Chemical Society , 1996
14.
Solid-Phase Chemical-Enzymic Synthesis of Glycopeptides and Oligosaccharides
Schuster M., Wang P., Paulson J.C., Wong C.
Journal of the American Chemical Society , 1994
18.
A PEGA resin for use in the solid-phase chemical–enzymatic synthesis of glycopeptides
Meldal M., Auzanneau F., Hindsgaul O., Palcic M.M.
Journal of the Chemical Society Chemical Communications , 1994
19.
Solid phase synthesis of oligosaccharides
Adinolfi M., Barone G., Napoli L.D., Iadonisi A., Piccialli G.
Tetrahedron Letters , 1996
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
24.
Glycosylation on the Merrifield Resin Using Anomeric Sulfoxides
Yan L., Taylor C.M., Goodnow R., Kahne D.
Journal of the American Chemical Society , 1994
25.
Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method.
Schmidt R.R., Kinzy W.
Advances in Carbohydrate Chemistry and Biochemistry , 1994
26.
A Strategy for the Solid-Phase Synthesis of Oligosaccharides
Danishefsky S.J., McClure K.F., Randolph J.T., Ruggeri R.B.
Science , 1993
29.
Synthèse du nigérose et du laminarabiose sur polymère support
Excoffier G., Gagnaire D.Y., Vignon M.R.
Carbohydrate Research , 1976
30.
Polymer-supported solution synthesis of oligosaccharides
Douglas S.P., Whitfield D.M., Krepinsky J.J.
Journal of the American Chemical Society , 1991
35.
Enzymic synthesis of N-acetyllactosamine on a soluble, light-sensitive polymer.
Wiemann T., Taubken N., Zehavi U., Thiem J.
Carbohydrate Research , 1994
36.
Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier
37.
Tetrahedron report number 218
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
A NEW METHOD FOR THE SOLID PHASE SYNTHESIS OF OLIGOSACCHARIDES
40.
Oligosaccharide Synthesis on Controlled-Pore Glass as Solid Phase Material
Heckel A., Mross E., Jung K., Rademann J., Schmidt R.R.
Synlett , 1998
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
Polymer-Supported Oligosaccharides via n-Pentenyl Glycosides:  Methodology for a Carbohydrate Library,1
Rodebaugh R., Joshi S., Fraser-Reid B., Geysen H.M.
Journal of Organic Chemistry , 1997
48.
Sulfonamidoglycosylation of glycals. A route to oligosaccharides with 2-aminohexose subunits
Griffith D.A., Danishefsky S.J.
Journal of the American Chemical Society , 1990
49.
Azaglycosylation of complex stannyl alkoxides with glycal-derived iodo sulfonamides: a straightforward synthesis of sialyl-Lewis X antigen and other oligosaccharide domains
Danishefsky S.J., Koseki K., Griffith D.A., Gervay J., Peterson J.M., McDonald F.E., Oriyama T.
Journal of the American Chemical Society , 1992
50.
Polymer‐supported solution synthesis of a heptaglucoside having phytoalexin elicitor activity
Verduyn R., van der Klein P.A., Douwes M., van der Marel G.A., van Boom J.H.
Recueil des Travaux Chimiques des Pays-Bas , 1993
51.
Conformation-dependent O-glycosylation of threonine-containing dipeptides
53.
Solid-phase synthesis of glycopeptides: Glycosylation of resin-bound serine-peptides by 3,4,6-tri-o-acetyl-D-glucose-oxazoline
Hollósi M., Kollát E., Laczkó I., Medzihradszky K.F., Thurin J., Otvös L.
Tetrahedron Letters , 1991
54.
A new procedure for the preparation of oligosaccharide oxazolines.
Nakabayashi S., Warren C.D., Jeanloz R.W.
Carbohydrate Research , 1986
55.
57.
Ježek J., Straka R., Krchňák V., Ryba M., Rotta J., Mayer P., Zaoral M.
Collection of Czechoslovak Chemical Communications , 2010
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
Solid phase synthesis of mono- and di-saccharide-containing glycopeptides
Lüning B., Norberg T., Tejbrant J.
Journal of the Chemical Society Chemical Communications , 1989
65.
A convenient procedure for the preparation of fully-protected C-terminal glycopeptides
Bauman A.C., Broderick J.S., Dacus R.M., Grover D.A., Trzupek L.S.
Tetrahedron Letters , 1993
66.
Pentafluorophenyl esters for the temporary protection of the α-carboxy group in solid phase glycopeptide synthesis
70.
70
N. Bubnov
Biofizika , 1960
71.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
Bielfeldt T., Peters S., Meldal M., Bock K., Paulsen H.
1992
80.
Total synthesis of B-chain of human α2HS glycoprotein
Nakahara Y., Nakahara Y., Ito Y., Ogawa T.
Tetrahedron Letters , 1997
81.
Comparison of N-Dts and N-Aloc in the solid-phase syntheses of O-GlcNAc glycopeptide fragments of RNA-polymerase II and mammalian neurofilaments
Meinjohanns E., Vargas-Berenguel A., Meldal M., Paulsen H., Bock K.
Journal of the Chemical Society Perkin Transactions 1 , 1995
82.
Solid-phase glycopeptide synthesis of tyrosine-glycosylated glycogenin fragments as substrates for glucosylation by glycogenin
Jansson A.M., Jensen K.J., Meldal M., Lomako J., Lomako W.M., Olsen C.E., Bock K.
Journal of the Chemical Society Perkin Transactions 1 , 1996
83.
Solid-phase synthesis of a fucosylated glycopeptide of human factor IX with a fucose-α-(1→O)-serine linkage
Peters S., Lowary T.L., Hindsgaul O., Meldal M., Bock K.
Journal of the Chemical Society Perkin Transactions 1 , 1995
85.
Synthesis of glycosylated peptide templates containing 6′-O-phosphorylated mannose disaccharides and their binding to the cation-independent mannose 6-phosphate receptor
Christensen M.K., Meldal M., Bock K., Cordes H., Mouritsen S., Elsner H.
Journal of the Chemical Society Perkin Transactions 1 , 1994
88.
A new simple synthesis of amino sugar β-d-glycosylamines
Likhosherstov L.M., Novikova O.S., Derevitskaja V.A., Kochetkov N.K.
Carbohydrate Research , 1986
91.
Synthesis of a glycopeptide carrying a N-linked core pentasaccharide.
Matsuo I., Nakahara Y., Ito Y., Nukada T., Nakahara Y., Ogawa T.
Bioorganic and Medicinal Chemistry , 1995
92.
New solid-phase oligosaccharide synthesis on glycopeptides bound to a solid phase
Paulsen H., Schleyer A., Mathieux N., Meldal M., Bock K.
Journal of the Chemical Society Perkin Transactions 1 , 1997
94.
Chemoenzymic Preparation of a Glycoconjugate Polymer Having a Sialyloligosaccharide: Neu5Acα(2→3)Galβ(1→4)GlcNAc
Nishimura S.I., Lee K.B., Matsuoka K., Lee Y.C.
Biochemical and Biophysical Research Communications , 1994
96.
Chemical and enzymatic synthesis of multivalent sialoglycopeptides.
Unverzagt C., Kelm S., Paulson J.C.
Carbohydrate Research , 1994
97.
Enzymic glycosphingolipid synthesis on polymer supports.
Zehavi U., Herchman M., Schmidt R.R., B�r T.
Glycoconjugate Journal , 1990
98.
Preparation of a fragment of the cell wall teichoic acid of Bacillus licheniformis atcc 9945 via a solid phase approach
Westerduin P., Veeneman G.H., Pennings Y., van der Marel G.A., van Boom J.H.
Tetrahedron Letters , 1987
99.
Synthesis of fragments of the capsular polysaccharide of Haemophilus influenzae type b: Part IIII-3. A solid-phase synthesis of a spacer-containing ribosylribitol phosphate hexamer
Elie C.J., Muntendam H.J., van den Elst H., van der Marel G.A., van Boom J.H., Hoogerhout P.
Recueil des Travaux Chimiques des Pays-Bas , 2010
101.
Solid-phase synthesis of a cell-wall component of Haemophilus (Actinobacillus) pleuropneumoniae serotype 2
Veeneman G.H., Brugghe H.F., van den Elst H., van Boom J.H.
Carbohydrate Research , 1990
102.
Combinatorial chemistry
Lowe G.
Chemical Society Reviews , 1995
103.
Preparation of Oligosaccharide Units Library and Its Utilization
Murata T., Usui T.
Bioscience, Biotechnology and Biochemistry , 1997
104.
Parallel Synthesis and Screening of a Solid Phase Carbohydrate Library
Liang R., Yan L., Loebach J., Ge M., Uozumi Y., Sekanina K., Horan N., Gildersleeve J., Thompson C., Smith A., Biswas K., Still W.C., Kahne D.
Science , 1996
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958