Synthesis

Automated Synthesis of Algal Fucoidan Oligosaccharides

Conor J. Crawford, Mikkel Schultz-Johansen, Phuong Luong, Silvia Vidal-Melgosa, Jan-Hendrik Hehemann, and Peter H. Seeberger*

J. Am. Chem. Soc. 2024, 146, 27, 18320–18330

Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly

Imlirenla Pongener, Eric T. Sletten, José Danglad-Flores, Peter H. Seeberger and Gavin J. Miller*

Org. Biomol. Chem., 2024, 22, 1395.

Merging Solid‐Phase Peptide Synthesis and Automated Glycan Assembly to Prepare Lipid‐Peptide‐Glycan Chimeras

Manuel G. Ricardo and Peter H. Seeberger

Chem. Eur. J. 2023, 29, e202301678.

Automated Glycan Assembly of Mycobacterial Hexaarabinofuranoside and Docosasaccharide Arabinan (Araf23) Motifs found on Mycobacterium tuberculosis

Narayana Murthy Sabbavarapu and  Peter H. Seeberger*

Chem. Eur. J. 2023, 29, e2023000

Automated glycan assembly of highly branched heptadecasaccharide repeating unit of arabinogalactan polysaccharide HH1-1 from Carthamus tinctorius

Narayana Murthy Sabbavarapu and Peter H. Seeberger *

Chem. Commun., 2023, 59, 4822-4824

Fluorine-Directed Automated Mannoside Assembly

Charlotte S. Teschers,  Ryan Gilmour

Angew. Chem. Int. Ed. 2023, 62, e202213304

Design, Synthesis, and Characterization of Stapled Oligosaccharides

Manuel G. Ricard, Emelie E. Reuber, Ling Yao, José Danglad-Flores, Martina Delbianco, and Peter H. Seeberger*

J. Am. Chem. Soc. 2022, 144, 40, 18429–18434

Deoxyfluorination tunes the aggregation of cellulose and chitin oligosaccharides and highlights the role of specific hydroxyl groups in the crystallization process

Giulio Fittolani, Surusch Djalali, Manishkumar A. Chaube, Theodore Tyrikos-Ergas‡, Marlene C. S. Dal Colle, Andrea Grafmüller, Peter H. Seeberger, and Martina Delbianco*

Org. Biomol. Chem., 2022, 20, 8228-8235

On resin synthesis of sulfated oligosaccharides

Theodore Tyrikos-Ergas, Eric T. Sletten, Jhih-Yi Huang, Peter H. Seeberger and Martina Delbianco*

Chem. Sci., 2022, 13, 2115

Expedited synthesis of mannose-6-phosphate containing oligosaccharides

Eric T. Sletten, Jose Danglad-Flores, Sabrina Leichnitz, A. Abragam Joseph,Peter H. Seeberger

Carb. Res. 2022, 511, 108489

Automated Assembly of Starch and Glycogen Polysaccharides

Yuntao Zhu, Martina Delbianco, and Peter H. Seeberger*

 

J. Am. Chem. Soc. 2021, 143, 26, 9758–9768

Automated Glycan Assembly of Oligogalactofuranosides Reveals the Influence of Protecting Groups on Oligosaccharide Stability

Narayana Murthy Sabbavarapu and Peter H. Seeberger*
 

J. Org. Chem. 2021, 86, 10, 7280

Automated Glycan Assembly of 19F-labeled Glycan Probes Enables High-Throughput NMR Studies of Protein–Glycan Interactions

Giulio Fittolani, Elena Shanina, Mónica Guberman, Peter H. Seeberger, Christoph Rademacher, Martina Delbianco

 

Angew. Chem. Int. Ed. 2021, 60, 13302

Systematic structural characterization of chitooligosaccharides enabled by Automated Glycan Assembly

Theodore Tyrikos‐Ergas, Vittorio Bordoni, Giulio Fittolani, Manishkumar A. Chaube, Andrea Grafmüller, Peter H. Seeberger, Martina Delbianco
 

Chem. Eur. J. 2021, 27, 2321

Automated glycan assembly of peptidoglycan backbone fragments

Pietro Dallabernardina, Valentina Benazzi, Jon D. Laman, Peter H. Seeberger, Felix F. Loeffler
 

Org. Biomol. Chem., 2021, 19, 9829

Total synthesis of polysaccharides by automated glycan assembly

A. Abragam Joseph, Alonso Pardo-Vargas, Peter H. Seeberger
 

J. Am. Chem. Soc. 2020, 142, 19, 8561

Automated access to well-defined ionic oligosaccharides

Yuntao Zhu, Theodore Tyrikos-Ergas, Kevin Schiefelbein, Andrea Grafmüller, Peter H. Seeberger, Martina Delbianco
 

Org. Biomol. Chem., 2020, 18, 1349

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

Alonso Pardo-Vargas, Priya Bharate, Martina Delbianco, Peter H. Seeberger
 

Beilstein J. Org. Chem. 2019, 15, 2936

Systematic hydrogen‐bond manipulations to establish polysaccharide structure–property correlations

Yang Yu, Theodore Tyrikos‐Ergas, Yuntao Zhu, Giulio Fittolani, Vittorio Bordoni, Ankush Singhal, Richard J. Fair, Andrea Grafmüller, Peter H. Seeberger, Martina Delbianco
 

Angew. Chem. 2019, 131, 13261

Using automated glycan assembly (AGA) for the practical synthesis of heparan sulfate oligosaccharide precursors

Darshita Budhadev, Karinna Saxby, Julia Walton, Gideon Davies, Peter C. Tyler, Ralf Schwörer* and Martin A. Fascione*
 

Org. Biomol. Chem., 2019, 17, 1817

Automated glycan assembly of Lewis type I and II oligosaccharide antigens

Mónica Guberman, Maria Bräutigam, Peter H. Seeberger
 

Chem. Sci., 2019, 10, 5634-5640

A Capping Step During Automated Glycan Assembly Enables Access to Complex Glycans in High Yield

Yang Yu, Andrew Kononov, Martina Delbianco, Peter H. Seeberger
 

Chem. Eur. J. 2018, 24, 6075

Well-defined oligo-and polysaccharides as ideal probes for structural studies

Martina Delbianco, Andrew Kononov, Ana Poveda, Yang Yu, Tammo Diercks, Jesus Jimenez-Barbero, Peter H. Seeberger
 

J. Am. Chem. Soc. 2018, 140, 16, 5421

Active Site Mapping of Xylan‐Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly

Deborah Senf, Colin Ruprecht, Goswinus HM de Kruijff, Sebastian O Simonetti, Frank Schuhmacher, Peter H Seeberger, Fabian Pfrengle
 

Mixed-Linkage Glucan Oligosaccharides Produced by Automated Glycan Assembly Serve as Tools To Determine the Substrate Specificity of Lichenase

Pietro Dallabernardina, Frank Schuhmacher, Peter H. Seeberger, Fabian Pfrengle
 

Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly

Max P. Bartetzko, Frank Schuhmacher, Peter H. Seeberger, Fabian Pfrengle
 

Automated glycan assembly of oligo-N-acetyllactosamine and keratan sulfate probes to study virus-glycan interactions

Heung Sik Hahm, Felix Broecker, Fumiko Kawasaki, Mario Mietzsch, Regine Heilbronn, Minoru Fukuda, Peter H. Seeberger
 

Pushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside

K. Naresh, F. Schumacher, H. S. Hahm and P. H. Seeberger
 
Chem. Commun., 2017, 53, 9085

Automated glycan assembly of branched β-(1, 3)-glucans to identify antibody epitopes

MW Weishaupt, HS Hahm, A Geissner, Peter H Seeberger
 
Chem. Commun., 2017, 53, 3591

Cyanopivaloyl Ester in the Automated Solid-Phase Synthesis of Oligorhamnans

Anne Geert Volbeda, Jeanine van Mechelen, Nico Meeuwenoord, Herman S. Overkleeft, Gijsbert A. van der Marel, and Jeroen D. C. Codée*

Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages

Heung Sik Hahm, Mattan Hurevich, Peter H Seeberger
 

Automated glycan assembly of complex oligosaccharides related to blood group determinants

Heung Sik Hahm, Chien-Fu Liang, Chian-Hui Lai, Richard J Fair, Frank Schuhmacher, Peter H Seeberger
 

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

Markus W Weishaupt, Stefan Matthies, Mattan Hurevich, Claney L Pereira, Heung Sik Hahm, Peter H Seeberger
 

Automated glycan assembly of xyloglucan oligosaccharides

Pietro Dallabernardina, Frank Schuhmacher, Peter H Seeberger, Fabian Pfrengle
 

Automated glycan assembly of oligosaccharides related to arabinogalactan proteins

Max P Bartetzko, Frank Schuhmacher, Heung Sik Hahm, Peter H Seeberger, Fabian Pfrengle
 

Automated synthesis of arabinoxylan‐oligosaccharides enables characterization of antibodies that recognize plant cell wall glycans

Deborah Schmidt, Frank Schuhmacher, Andreas Geissner, Peter H Seeberger, Fabian Pfrengle
 

Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to α (2, 3)-sialylated glycans

Richard J Fair, Heung Sik Hahm, Peter H Seeberger
 
Chem. Commun., 2015, 51, 6183

Modular automated solid phase synthesis of dermatan sulfate oligosaccharides

Jeyakumar Kandasamy, Frank Schuhmacher, Heung Sik Hahm, James C Klein, Peter H Seeberger
 

Automated glycopeptide assembly by combined solid-phase peptide and oligosaccharide synthesis

Mattan Hurevich and  Peter H. Seeberger
 

Automated solid‐phase synthesis of a β‐(1, 3)‐glucan dodecasaccharide

Markus W Weishaupt, Stefan Matthies, Peter H Seeberger
 

Automated solid-phase synthesis of chondroitin sulfate glycosaminoglycans

Steffen Eller, Mayeul Collot, Jian Yin, Heung Sik Hahm, Peter H Seeberger
 

Automated polysaccharide synthesis: assembly of a 30mer mannoside

Oliviana Calin, Steffen Eller, Peter H Seeberger
 

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

Mayeul Collot, Steffen Eller, Markus Weishaupt, Peter H Seeberger
 

Automated solid phase synthesis of oligoarabinofuranosides

Jeyakumar Kandasamy, Mattan Hurevich, Peter H Seeberger
 

Automated synthesis of sialylated oligosaccharides

Davide Esposito, Mattan Hurevich, Bastien Castagner, Cheng-Chung Wang, Peter H Seeberger
 

Automated Solid‐Phase Synthesis of β‐Mannuronic Acid Alginates

Marthe TC Walvoort, Hans van den Elst, Obadiah J Plante, Lenz Kröck, Peter H Seeberger, Herman S Overkleeft, Gijsbert A van der Marel, Jeroen DC Codée
 

Streamlined access to conjugation-ready glycans by automated synthesis

Lenz Kröck, Davide Esposito, Bastien Castagner, Cheng-Chung Wang, Pascal Bindschädler, Peter H Seeberger
 

Automated solid‐phase synthesis of protected oligosaccharides containing β‐mannosidic linkages

Jeroen DC Codée, Lenz Kröck, Bastien Castagner, Peter H Seeberger
 

Cap-and-tag solid phase oligosaccharide synthesis

Frédéric R Carrel, Peter H Seeberger
 

Automated synthesis of lipomannan backbone α (1-6) oligomannoside via glycosyl phosphates: glycosyl tricyclic orthoesters revisited

Xinyu Liu, Reiko Wada, Siwarutt Boonyarattanakalin, Bastien Castagner, Peter H Seeberger
 

Automated synthesis of the tumor-associated carbohydrate antigens Gb-3 and Globo-H: incorporation of α-galactosidic linkages

Daniel B Werz, Bastien Castagner, Peter H Seeberger
 

Automated Solid-Phase Synthesis of Protected Tumor-Associated Antigen and Blood Group Determinant Oligosaccharides

Kerry Routenberg Love, Peter H Seeberger
 

Automated synthesis of a protected N-linked glycoprotein core pentasaccharide

Daniel M Ratner, Erika R Swanson, Peter H Seeberger
 

Toward the automated solid-phase synthesis of oligoglucosamines: systematic evaluation of glycosyl phosphate and glycosyl trichloroacetimidate building blocks

Luis G Melean, Kerry R Love, Peter H Seeberger
 

Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis

Michael C Hewitt, Daniel A Snyder, Peter H Seeberger
 

Linker influence on the stereochemical outcome of glycosylations utilizing solid support-bound glycosyl phosphates

Diana K Hunt, Peter H Seeberger
 

Oligosaccharide synthesis in solution and on solid support with glycosyl phosphates

Emma R Palmacci, Obadiah J Plante, Peter H Seeberger
 

“Cap‐Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid‐Phase Synthesis

Emma R Palmacci, Michael C Hewitt, Peter H Seeberger
 

Automated Solid-Phase Synthesis of a Branched Leishmania Cap Tetrasaccharide

Michael C Hewitt, Peter H Seeberger
 

Automated solid-phase synthesis of oligosaccharides

Obadiah J Plante, Emma R Palmacci, Peter H Seeberger
 

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