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Pure Appl. Chem., 1993, Vol. 65, No. 6, pp. 1223-1232

http://dx.doi.org/10.1351/pac199365061223

Glycopeptides of biological interest: A challenge for chemical synthesis

H. Kunz

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  • Pedersen Søren L., Tofteng A. Pernille, Malik Leila, Jensen Knud J.: Microwave heating in solid-phase peptide synthesis. Chemical Society Review 2012, 41, 1826. <http://dx.doi.org/10.1039/c1cs15214a>
  • Xue Jie, Guo Min, Gu Guofeng, Guo Zhongwu: A Facile Synthesis of N γ-Glycosyl Asparagine Conjugates and Short N-Linked Glycopeptides. J Carbohydr Chem 2012, 31, 105. <http://dx.doi.org/10.1080/07328303.2011.633723>
  • KUNZ H.: ChemInform Abstract: Glycopeptides of Biological Interest: A Challenge for Chemical Synthesis. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199336312>
  • Zhu Xiangming, Schmidt Richard R.: Neue Prinzipien für die Bildung von glycosidischen Bindungen. Angew Chem 2009, 121, 1932. <http://dx.doi.org/10.1002/ange.200802036>
  • Zhu Xiangming, Schmidt Richard R.: New Principles for Glycoside-Bond Formation. Angew Chem Int Ed 2009, 48, 1900. <http://dx.doi.org/10.1002/anie.200802036>
  • Nguyen Thanh Binh, Vuong Thi Minh Ha, Martel Arnaud, Dhal Robert, Dujardin Gilles: Practical asymmetric access to carboxy-differentiated aspartate derivatives via 1,3-dipolar cycloaddition of a nitrone with (R)-4-ethyl-N-vinyloxazolidin-2-one. Tet Asymm 2008, 19, 2084. <http://dx.doi.org/10.1016/j.tetasy.2008.08.020>
  • Álvarez-Micó Xavier, Calvete Mario J.F., Hanack Michael, Ziegler Thomas: A new glycosidation method through nitrite displacement on substituted nitrobenzenes. Carbohydrates Research 2007, 342, 440. <http://dx.doi.org/10.1016/j.carres.2006.11.017>
  • Shao Ning, Guo Zhongwu: Solution-Phase Synthesis with Solid-State Workup of an O-Glycopeptide with a Cluster of Cancer-Related T Antigens. Org Lett 2005, 7, 3589. <http://dx.doi.org/10.1021/ol0514193>
  • Bräse Stefan, Kirchhoff Jan H., Köbberling Johannes: Palladium-catalysed reactions in solid phase organic synthesis. Tetrahedron 2003, 59, 885. <http://dx.doi.org/10.1016/S0040-4020(02)01425-4>
  • Buchynskyy Andrij, Stembera Katherina, Knoll Dietmar, Vogel Stefan, Kempin Uwe, Biallaß (née Donnerstag) Astrid, Hennig Lothar, Findeisen Matthias, Müller Dietrich, Welzel Peter: Synthesis of tools for raising antibodies against moenomycin epitopes and initial immunological studies. Tetrahedron 2002, 58, 7741. <http://dx.doi.org/10.1016/S0040-4020(02)00838-4>
  • Dondoni Alessandro, Marra Alberto, Scherrmann Marie-Christine, Bertolasi Valerio: Chemical Synthesis of Linear and Cyclic Unnatural Oligosaccharides by Iterative Glycosidation of Ketoses. Chem Eur J 2001, 7, 1371. <http://dx.doi.org/10.1002/1521-3765(20010401)7:7<1371::AID-CHEM1371>3.0.CO;2-J>
  • Koóš Miroslav, Steiner Bohumil, Mičová Júlia, Langer Vratislav, Ďurı́k Marián, Gyepesová Dalma: Synthesis and structure determination of some sugar amino acids related to alanine and 6-deoxymannojirimycin. Carbohydrates Research 2001, 332, 351. <http://dx.doi.org/10.1016/S0008-6215(01)00109-4>
  • Li Xiaoliu, Ohtake Hiro, Takahashi Hideyo, Ikegami Shiro: A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides. Tetrahedron 2001, 57, 4297. <http://dx.doi.org/10.1016/S0040-4020(01)00321-0>
  • Kovács László, Ősz Erzsébet, Domokos Valéria, Holzer Wolfgang, Györgydeák Zoltán: An easy access to anomeric glycosyl amides and imines(Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides. Tetrahedron 2001, 57, 4609. <http://dx.doi.org/10.1016/S0040-4020(01)00380-5>
  • Wen Showming, Guo Zhongwu: Unprotected Oligosaccharides as Phase Tags:  Solution-Phase Synthesis of Glycopeptides with Solid-Phase Workups. Org Lett 2001, 3, 3773. <http://dx.doi.org/10.1021/ol0101988>
  • Allen Jennifer R., Danishefsky Samuel J.: Vom Labor zur Klinik: vollsynthetische Antitumor-Impfstoffe auf Kohlenhydratbasis. Angew Chem 2000, 112, 882. <http://dx.doi.org/10.1002/(SICI)1521-3757(20000303)112:5<882::AID-ANGE882>3.0.CO;2-1>
  • Koóš Miroslav, Steiner Bohumil, Langer Vratislav, Gyepesová Dalma, Ďurı́k Marián: Preparation and structure determination of two sugar amino acids via corresponding hydantoin derivatives. Carbohydrates Research 2000, 328, 115. <http://dx.doi.org/10.1016/S0008-6215(00)00099-9>
  • Osborn Helen M.I., Khan Tariq H.: Recent developments in polymer supported syntheses of oligosaccharides and glycopeptides. Tetrahedron 1999, 55, 1807. <http://dx.doi.org/10.1016/S0040-4020(98)01200-9>
  • Lieberknecht Albrecht, Griesser Helmut, Krämer Bernd, Bravo Rodolfo D., Colinas Pedro A., Grigera Raúl J.: Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine. Tetrahedron 1999, 55, 6475. <http://dx.doi.org/10.1016/S0040-4020(99)00306-3>
  • Matsuo Ichiro, Isomura Megumi, Ajisaka Katsumi: Synthesis of an Asparagine-Linked Core Pentasaccharide by Means of Simultaneous Inversion Reactions. J Carbohydr Chem 1999, 18, 841. <http://dx.doi.org/10.1080/07328309908544039>
  • Dondoni Alessandro, Marra Alberto, Massi Alessandro: Stereoselective synthesis of the C-linked analogue of β-d-galactopyranosyl-l-serine. Tetrahedron 1998, 54, 2827. <http://dx.doi.org/10.1016/S0040-4020(98)83019-6>
  • Dondoni Alessandro, Massi Alessandro, Marra Alberto: Synthesis of ethylene isosteres of β-d-galactosyl- and β-d-glucosyl-l-asparagine. Tetrahetron Lett 1998, 39, 6601. <http://dx.doi.org/10.1016/S0040-4039(98)01376-8>
  • Werner R.Marshall, Williams Leonard M., Davis Jeffery T.: The Cglycosyl analog of an N-linked glycoamino acid. Tetrahetron Lett 1998, 39, 9135. <http://dx.doi.org/10.1016/S0040-4039(98)02065-6>
  • Burkhart Fred, Hoffmann Matthias, Kessler Horst: Stereoselektive Synthese eines C-glycosidischen Analogons desN-Glucoasparagins. Angew Chem 1997, 109, 1240. <http://dx.doi.org/10.1002/ange.19971091115>
  • Guo Zhong-Wu, Nakahara Yuko, Nakahara Yoshiaki, Ogawa Tomoya: Festphasensynthese des Glycopeptidteils des Antigens CD52 mit N-gebundenem Core-Pentasaccharid. Angew Chem 1997, 109, 1527. <http://dx.doi.org/10.1002/ange.19971091317>
  • McGarvey Glenn J., Wong Chi-Huey: Chemical, Enzymatic and Structural Studies in Molecular Glycobiology. Liebigs Ann /Recueil 1997, 1997, 1059. <http://dx.doi.org/10.1002/jlac.199719970604>
  • Ogawa Tomoya, Guo Zhong-Wu, Nakahara Yuko, Nakahara Yoshiaki: Solid-phase synthesis of a glycosylated peptide fragment of the IL-8 receptor containing two vicinal oligosaccharide chains. Carbohydrates Research 1997, 303, 373. <http://dx.doi.org/10.1016/S0008-6215(97)00180-8>
  • Guo Zhong-Wu, Nakahara Yoshiaki, Ogawa Tomoya: A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a key building block for the synthesis of complex N-linked glycopeptides. Tetrahetron Lett 1997, 38, 4799. <http://dx.doi.org/10.1016/S0040-4039(97)01036-8>
  • Arsequell Gemma, Valencia Gregorio: O-glycosyl α-amino acids as building blocks for glycopeptide synthesis. Tet Asymm 1997, 8, 2839. <http://dx.doi.org/10.1016/S0957-4166(97)00326-1>
  • Guo Zhong-Wu, Nakahara Yuko, Nakahara Yoshiaki, Ogawa Tomoya: Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate. biorg med chem 1997, 5, 1917. <http://dx.doi.org/10.1016/S0968-0896(97)00126-0>
  • Pohl Torsten, Waldmann Herbert: Enzymatische Synthese eines charakteristischen phosphorylierten und glycosylierten Peptidfragmentes der großen Untereinheit der RNA-Polymerase II aus Säugetieren. Angew Chem 1996, 108, 1829. <http://dx.doi.org/10.1002/ange.19961081531>
  • Hoffmann Matthias, Burkhart Fred, Hessler Gerhard, Kessler Horst: C-Glycoside Analogues ofN4-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine: Synthesis and conformational analysis of a cyclicC-glycopeptide. HCA 1996, 79, 1519. <http://dx.doi.org/10.1002/hlca.19960790602>
  • Nakahara Yoshiaki, Nakahara Yuko, Ogawa Tomoya: Solid-phase synthesis of an O-linked glycopeptide based on a benzyl-protected glycan approach. Carbohydrates Research 1996, 292, 71. <http://dx.doi.org/10.1016/S0008-6215(96)91027-7>
  • Live D. H., Kumar R. A., Beebe X., Danishefsky S. J.: Conformational influences of glycosylation of a peptide: A possible model for the effect of glycosylation on the rate of protein folding. Proceedings of the National Academy of Sciences 1996, 93, 12759. <http://dx.doi.org/10.1073/pnas.93.23.12759>
  • Wong C.-H., Halcomb Randall L., Ichikawa Yoshitaka, Kajimoto Tetsuya: Enzyme in der organischen Synthese: das Problem der molekularen Erkennung von Kohlenhydraten (Teil 2). Angew Chem 1995, 107, 569. <http://dx.doi.org/10.1002/ange.19951070505>
  • Arsequell Gemma, Sàrries Núria, Valencia Gregorio: Synthesis of glycosylated hydroxyproline building blocks. Tetrahetron Lett 1995, 36, 7323. <http://dx.doi.org/10.1016/0040-4039(95)01509-G>
  • Kunz Horst, Kowalczyk Danuta, Braun Peter, Braum Günther: Enzymatische Hydrolyse hydrophiler Diethylenglycol- und Polyethylenglycolester von Peptiden und Glycopeptiden durch Lipasen. Angew Chem 1994, 106, 353. <http://dx.doi.org/10.1002/ange.19941060325>
  • Meldal Morten, Bock Klaus: A general approach to the synthesis ofO- andN-linked glycopeptides. Glycoconjugate J 1994, 11, 59. <http://dx.doi.org/10.1007/BF00731144>
  • Kates Steven A., de la Torre Beatriz G., Eritja Ramon, Albericio Fernando: Solid-phase N-glycopeptide synthesis using allyl side-chain protected Fmoc-amino acids. Tetrahetron Lett 1994, 35, 1033. <http://dx.doi.org/10.1016/S0040-4039(00)79958-8>
  • Meldal Morten: Recent developments in glycopeptide and oligosaccharide synthesis. curr opin struct biol 1994, 4, 710. <http://dx.doi.org/10.1016/S0959-440X(94)90169-4>
  • Dupradeau François-Yves, Stroud Mark R., Boivin Diane, Li Linsong, Hakomori Sen-itiroh, Singhal Anil K., Toyokuni Tatsushi: Solid-phase synthesis and immunoreactivity of penta-O-(N-acetyl-α-D-galactosaminyl)-MUC1 eicosapeptide, a glycosylated counter part of the highly immunogenic tandem repeat sequence of carcinoma-associated mucin. Biorg Med Chem Lett 1994, 4, 1813. <http://dx.doi.org/10.1016/S0960-894X(01)80376-0>
  • Toyokuni Tatsushi, Hakomori Sen-itiroh, Singhal Anil K.: Synthetic carbohydrate vaccines: Synthesis and immunogenicity of Tn antigen conjugates. biorg med chem 1994, 2, 1119. <http://dx.doi.org/10.1016/S0968-0896(00)82064-7>
  • Harrison Allen W., Fisher Jed F., Guido David M., Couch Sally J., Lawson Judy A., Sutter Dorothy M., Williams Mark V., DeGraaf Garry L., Rogers John E., Pals Donald T.: Appraisal of a glycopeptide cloaking strategy for a therapeutic oligopeptide: Glycopeptide analogs of the renin inhibitor ditekiren. Bioorganic & Medicinal Chemistry 1994, 2, 1339. <http://dx.doi.org/10.1016/S0968-0896(00)82086-6>