Publications Group Pfrengle

I. Álvarez-Martínez, C. Ruprecht, D. Senf, HT. Wang, BR. Urbanowicz, F. Pfrengle, "Chemo-Enzymatic Synthesis of Long-Chain Oligosaccharides for Studying Xylan-Modifying Enzymes” Chemistry 2023; 29(26):e202203941

C. Ruprecht, M. Blaukopf, F. Pfrengle*, "Synthetic fragments of plant polysaccharides as tools for cell wall biology" Curr. Opin. Chem. Biol. 2022; 71, 102208

M.A. Chaube, N. Trattnig, D.H. Lee, Y. Belkhadir, F. Pfrengle*, “Synthesis of Fungal Cell Wall Oligosaccharides and Their Ability to Trigger Plant Immune Responses” Eur. J. Org. Chem. 2022, 27, e202200313

M. Islam, B.M. Arlan, F. Pfrengle, S.A. Smith, J.C. Paulson*, “Suppressing Immune Responses using Siglec-Ligand-Decorated anti-Receptor Antibodies” J. Am. Chem. Soc. 2022, 144(21), 9302-9311

C. Ruprecht, F. Pfrengle*, "Synthetic Plant Glycan Microarrays as Tools for Plant Biology" in Kilcoyne M., Gerlach J.Q. (eds) Glycan Microarrays. Methods in Molecular Biology 2022, vol 2460. Humana, New York, NY.

F. Pfrengle, "Kohlenhydrate" in Trendberichte Organische Chemie. Nachr. Chem. 2022, 70, 42-69

D. Rebaque, I. del Hierro, G. López, L. Bacete, F. Vilaplana, P. Dallabernardina, F. Pfrengle, L. Jordá, A. Sánchez-Vallet, R. Pérez, F. Brunner, A. Molina, H. Mélida*, "Cell wall-derived mixed-linked β-1,3/1,4-glucans trigger immune responses and disease resistance in plants"
Plant Journal 2021, 106, 601-615

M. J. Soto, P. K. Prabhakar, H.-T. Wang, J. Backe, D. Chapla, M. Bartetzko, I. M. Black, P. Azadi, M. J. Peña, F. Pfrengle, K. W. Moremen, B. R. Urbanowicz, M. G. Hahn*, "AtFUT4 and AtFUT6 Are Arabinofuranose-Specific Fucosyltransferases"
Front. Plant Sci. 2021, 12, Article 589518

R. Strasser, G. Seifert, M. S. Doblin, K. L. Johnson, C. Ruprecht, F. Pfrengle, A. Bacic, J. M. Estevez*, "Cracking the “Sugar Code”: A Snapshot of N- and O-Glycosylation Pathways and Functions in Plants Cells"
Front. Plant Sci. 2021, 12, Article 640919

H. Mélida, L. Bacete, C. Ruprecht, D. Rebaque, I. del Hierro, G. López, F. Brunner, F. Pfrengle, A. Molina*, "Arabinoxylan-Oligosaccharides Act as Damage Associated Molecular Patterns in Plants Regulating Disease Resistance"
Front. Plant Sci. 2020, 11, Article 1210

P. J. Smith, M. E. Ortiz-Soto, C. Roth, W. J. Barnes, J. Seibel, B. R. Urbanowicz, F. Pfrengle* "Enzymatic Synthesis of Artificial Polysaccharides"
ACS Sustainable Chem. Eng. 2020, 8, 32, 11853–11871

F. Pfrengle*,
"Automated Glycan Assembly of Plant Cell Wall Oligosaccharides"
in: Popper Z. (eds): The Plant Cell Wall, Methods in Molecular Biology 2020, vol 2149. Humana, New York, NY

C. Ruprecht, M. P. Bartetzko, D. Senf, A. Lakhina, P. J. Smith, M. J. Soto, H. Oh, J.-Y. Yang, D. Chapla, D. Varon Silva, M. H. Clausen, M. G. Hahn, K. W. Moremen, B. R. Urbanowicz*, F. Pfrengle*
“A Glycan Array‐Based Assay for the Identification and Characterization of Plant Glycosyltransferases”
Angew. Chem. Int. Ed. 2020, 59 (30), 12493-12498

Y. Pauchet*, C. Ruprecht, F. Pfrengle
"Analyzing the Substrate Specificity of a Class of Long‐Horned‐Beetle‐Derived Xylanases by Using Synthetic Arabinoxylan Oligo‐ and Polysaccharides”
ChemBioChem 2020, 21, 1517-1525

C. Ruprecht, A. Geissner, P. H. Seeberger, F. Pfrengle*
"Practical considerations for printing high-density glycan microarrays to study weak carbohydrate-protein interactions"
Carb. Res. 2019, 481, 31-35.

29  M. P. Bartetzko, F. Pfrengle*
“Automated Glycan Assembly of Plant Oligosaccharides and Their Application in Cell Wall Biology“
ChemBioChem 2019, 20, 877-885 (review).

F. Pfrengle*
Solid-phase glycan synthesis. In “Synthetic glycomes”
The Royal Society of Chemistry, 2019, 331-355 (book chapter).

D. Senf, C. Ruprecht, S. Kishani, A. Matic, G. Toriz, P. Gatenholm, L. Wagberg, F. Pfrengle*,
“Tailormade Polysaccharides with Defined Branching Patterns: Enzymatic Polymerization of Arabinoxylan Oligosaccharides”
Angew. Chem. Int. Ed. 2018, 57, 11987-11992.

C. Ruprecht, P. Dallabernardina, P. J. Smith, B. R. Urbanowicz, F. Pfrengle*
"Analyzing Xyloglucan Endotransglycosylases by Incorporation of Synthetic Oligosaccharides into Plant Cell Walls"
ChemBioChem 2018, 19, 793-798.

F. Pfrengle*, P. H. Seeberger*
Orthogonally protected building blocks for automated glycan assembly.
In “Protecting Groups: Strategies and Applications in Carbohydrate Chemistry”, WILEY-VCH, 2018, 451-471 (book chapter).

 P. Dallabernardina, C. Ruprecht, P. J. Smith, M. G. Hahn, B. R. Urbanowicz, F. Pfrengle*
"Automated glycan assembly of galactosylated xyloglucan oligosaccharides and their recognition by plant cell wall glycan-directed antibodies"
Org. Biomol. Chem. 2017, 15, 9996-10000.

M. C. F. Andersen, I. Boos, C. Ruprecht, W. G. T. Willats, F. Pfrengle, M. H. Clausen,
"Synthesis and Application of Branched Type II Arabinogalactans"
J. Org. Chem. 2017, 82, 12066-12084.

C. Ruprecht, M. P. Bartetzko, D. Senf, P. Dallabernadina, I. Boos, M. C. F. Andersen, T. Kotake, J. P. Knox, M. G. Hahn, M. H. Clausen, F. Pfrengle*
A synthetic glycan microarray enables epitope mapping of plant cell wall glycan-directed antibodies
Plant Physiol. 2017, 175, 1094-1104.

F. Pfrengle*
Synthetic Plant Glycans
Curr. Opin. Chem. Biol. 2017, 40, 145-151 (review).

D. Senf, C. Ruprecht, Goswinus H. M. de Kruijff, S. O. Simonetti, F. Schuhmacher, P. H. Seeberger, F. Pfrengle*
Active Site-Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly
Chem. Eur. J. 2017, 23, 3197-3205.

M. P. Bartetzko, F. Schuhmacher, P. H. Seeberger, F. Pfrengle*
Determining Substrate Specificities of β1,4-Endo-Galactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly
J. Org. Chem. 2017, 82, 1842-1850.

P. Dallabernardina, F. Schuhmacher, P. H. Seeberger, F. Pfrengle*
Mixed-Linkage Glucan Oligosaccharides Produced by Automated Glycan Assembly Serve as Tools to Determine the Substrate Specificity of Lichenase
Chem. Eur. J. 2017, 23, 3191-3196.

M. Wilsdorf, D. Schmidt, M. P. Bartetzko, P. Dallabernardina, F. Schuhmacher, P. H. Seeberger, F. Pfrengle*
A traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends
Chem. Commun. 2016, 52, 10187-10189.

P. Dallabernardina, F. Schuhmacher, P. H. Seeberger, F. Pfrengle*
Automated Glycan Assembly of Xyloglucan Oligosaccharides
Org. Biomol. Chem. 2016, 14, 309-313.

M. P. Bartetzko, F. Schuhmacher, H. S. Hahm, P. H. Seeberger, F. Pfrengle*
Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins
Org. Lett. 2015, 17, 4344-4347.

D. Schmidt, F. Schuhmacher, A. Geissner, P. H. Seeberger, F. Pfrengle*
Automated Synthesis of Arabinoxylan-Oligosaccharides Enables Characterization of Antibodies that Recognize Plant Cell Wall Glycans
Chem. Eur. J. 2015, 21, 5709-5713.

M. S. Macauley, F. Pfrengle, C. Rademacher, C. M. Nycholat, A. J. Gale, A. von Drygalski, J. C. Paulson
Antigenic liposomes displaying CD22 ligands induce antigen-specific B cell apoptosis
J. Clin. Invest. 2013, 123, 3074-3083. Highlighted in: L. Nitschke N. Engl. J. Med. 2013, 369, 1373-74.

F. Pfrengle, M. S. Macauley, N. Kawasaki, J. C. Paulson,
Copresentation of Antigen and Ligands of Siglec-G Induces B Cell Tolerance Independent of CD22
J. Immunol. 2013, 191, 1724-1731.

T. Lechel, F. Pfrengle, H.-U. Reissig, R. Zimmer
Three Carbons for Complexity! Recent Developments on Palladium-Catalyzed Reactions of Allenes
ChemCatChem 2013, 5, 2100-2130 (review).

M. Roskamp, S. Enders, F. Pfrengle, S. Yekta, V. Dekaris, J. Dernedde, H.-U. Reissig, S. Schlecht
Multivalent Interaction and Selectivities in Selectin Binding of Functionalized Gold Colloids Decorated with Carbohydrate Mimetics
Org. Biomol. Chem. 2011, 9, 7448-7456.

F. Pfrengle, H.-U. Reissig
Addition of lithiated enol ethers to nitrones and subsequent Lewis acid induced cyclizations to enantiopure 3,6-dihydro-2H-pyrans - an approach to carbohydrate mimetics
Beilstein J. Org. Chem. 2010, 6, No. 75.

F. Pfrengle, H.-U. Reissig
Internally Protected Amino Sugar Equivalents from Enantiopure 1,2-Oxazines: Synthesis of Variably Configured Carbohydrates with C-Branched Amino Sugar Units
Chem. Eur. J. 2010, 16, 11915-11925.

F. Pfrengle, H.-U. Reissig
Amino sugars and their mimetics via 1,2-oxazines
Chem. Soc. Rev. 2010, 39, 549-557 (review).

F. Pfrengle, D. Lentz, H.-U. Reissig,
A New Ring Closure Approach to Enantiopure 3,6-Dihydro-2H-pyrans – Stereodivergent Access to Carbohydrate Mimetics
Org. Lett. 2009, 11, 5534-5537.

A. Al-Harrasi, F. Pfrengle, V. Prisyashnyuk, S. Yekta, P. Koóš, H.-U. Reissig
Enantiopure Aminopyrans by a Lewis Acid Promoted Rearrangement of 1,2-Oxazines: Versatile Building Blocks for Oligosaccharide and Sugar Amino Acid Mimetics
Chem. Eur. J. 2009, 15, 11632-11641.

F. Pfrengle, D. Lentz, H.-U. Reissig
Stereodivergent De Novo Synthesis of Branched Amino Sugars by Lewis Acid Promoted Rearrangement of 1,2-Oxazines
Angew. Chem. Int. Ed. 2009, 48, 3165-3169.

F. Pfrengle, A. Al-Harrasi, I. Brüdgam, H.-U. Reissig
Unusual Heterocyclic Skeletons via Lewis Acid Promoted Rearrangements of 1,3-Dioxolanyl-Substituted 1,2-Oxazines
Eur. J. Org. Chem. 2009, 282-291.

F. Pfrengle, V. Dekaris, L. Schefzig, R. Zimmer, H.-U. Reissig
Indium Trichloride Mediated Cleavage of Acetonides in the Presence of Acid-Labile Functional Groups – Enhancing the Synthetic Utility of 1,3-Dioxolanyl-Substituted 1,2-Oxazines
Synlett 2008, 2965-2968. Highlighted: Synfacts 2009, 251.

F. Pfrengle, A. Al-Harrasi, H.-U. Reissig
Lewis Acid Promoted Rearrangements of 1,3-Dioxolanyl-Substituted 1,2-Oxazines into Novel Products with 1,3,6-Trioxa-7-azacyclopenta[cd]indene Skeletons
Synlett 2006, 3498-3500.

Qualification Work:

F. Pfrengle:
“Synthesis of Plant Glycans and Their Application in Biology”
Habilitationsschrift, Fachbereich Biologie, Chemie, Pharmazie der Freien Universität Berlin (2019).

F. Pfrengle:
„Synthese C-verzweigter Aminozucker und verwandter Kohlenhydratmimetika als potentielle Liganden multivalenter Konjugate“
Dissertation, Freie Universität Berlin (2010).


J. C. Paulson, M. S. Macauley, F. Pfrengle
Methods and Compositions for Treating Bleeding Disorders.
US Patent Application #20160060324.

Full list of publications