Literature DB >> 28396442

Automated glycan assembly using the Glyconeer 2.1 synthesizer.

Heung Sik Hahm1,2, Mark K Schlegel1,3, Mattan Hurevich1, Steffen Eller1, Frank Schuhmacher1,2, Johanna Hofmann2,4, Kevin Pagel2,4, Peter H Seeberger5,2.   

Abstract

Reliable and rapid access to defined biopolymers by automated DNA and peptide synthesis has fundamentally altered biological research and medical practice. Similarly, the procurement of defined glycans is key to establishing structure-activity relationships and thereby progress in the glycosciences. Here, we describe the rapid assembly of oligosaccharides using the commercially available Glyconeer 2.1 automated glycan synthesizer, monosaccharide building blocks, and a linker-functionalized polystyrene solid support. Purification and quality-control protocols for the oligosaccharide products have been standardized. Synthetic glycans prepared in this way are useful reagents as the basis for glycan arrays, diagnostics, and carbohydrate-based vaccines.

Entities:  

Keywords:  Glyconeer; automated synthesis; glycobiology; glycochemistry; oligosaccharide synthesis

Year:  2017        PMID: 28396442      PMCID: PMC5410834          DOI: 10.1073/pnas.1700141114

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  18 in total

1.  Automated polysaccharide synthesis: assembly of a 30mer mannoside.

Authors:  Oliviana Calin; Steffen Eller; Peter H Seeberger
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-22       Impact factor: 15.336

2.  Automated solid-phase synthesis of β-mannuronic acid alginates.

Authors:  Marthe T C Walvoort; Hans van den Elst; Obadiah J Plante; Lenz Kröck; Peter H Seeberger; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-14       Impact factor: 15.336

3.  Continuous photochemical cleavage of linkers for solid-phase synthesis.

Authors:  Mattan Hurevich; Jeyakumar Kandasamy; Bopanna M Ponnappa; Mayeul Collot; Daniel Kopetzki; D Tyler McQuade; Peter H Seeberger
Journal:  Org Lett       Date:  2014-03-11       Impact factor: 6.005

Review 4.  Toward automated oligosaccharide synthesis.

Authors:  Che-Hsiung Hsu; Shang-Cheng Hung; Chung-Yi Wu; Chi-Huey Wong
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-30       Impact factor: 15.336

5.  An automated multiplex oligonucleotide synthesizer: development of high-throughput, low-cost DNA synthesis.

Authors:  D A Lashkari; S P Hunicke-Smith; R M Norgren; R W Davis; T Brennan
Journal:  Proc Natl Acad Sci U S A       Date:  1995-08-15       Impact factor: 11.205

6.  Automated solid phase synthesis of oligoarabinofuranosides.

Authors:  Jeyakumar Kandasamy; Mattan Hurevich; Peter H Seeberger
Journal:  Chem Commun (Camb)       Date:  2013-01-31       Impact factor: 6.222

Review 7.  The envelope of mycobacteria.

Authors:  P J Brennan; H Nikaido
Journal:  Annu Rev Biochem       Date:  1995       Impact factor: 23.643

Review 8.  Oligosaccharide assembly by one-pot multi-step strategy.

Authors:  Yuhang Wang; Xin-Shan Ye; Li-He Zhang
Journal:  Org Biomol Chem       Date:  2007-05-22       Impact factor: 3.876

9.  Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.

Authors:  Heung Sik Hahm; Mattan Hurevich; Peter H Seeberger
Journal:  Nat Commun       Date:  2016-09-01       Impact factor: 14.919

Review 10.  Automated solid-phase peptide synthesis to obtain therapeutic peptides.

Authors:  Veronika Mäde; Sylvia Els-Heindl; Annette G Beck-Sickinger
Journal:  Beilstein J Org Chem       Date:  2014-05-22       Impact factor: 2.883

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  29 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

Review 3.  Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies.

Authors:  Tinghua Wang; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2019-05-02       Impact factor: 3.876

4.  Microbe-focused glycan array screening platform.

Authors:  Andreas Geissner; Anika Reinhardt; Christoph Rademacher; Timo Johannssen; João Monteiro; Bernd Lepenies; Michel Thépaut; Franck Fieschi; Jana Mrázková; Michaela Wimmerova; Frank Schuhmacher; Sebastian Götze; Dan Grünstein; Xiaoqiang Guo; Heung Sik Hahm; Jeyakumar Kandasamy; Daniele Leonori; Christopher E Martin; Sharavathi G Parameswarappa; Sandip Pasari; Mark K Schlegel; Hidenori Tanaka; Guozhi Xiao; You Yang; Claney L Pereira; Chakkumkal Anish; Peter H Seeberger
Journal:  Proc Natl Acad Sci U S A       Date:  2019-01-22       Impact factor: 11.205

Review 5.  The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.

Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

6.  Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans.

Authors:  Salvatore G Pistorio; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2019-05-17       Impact factor: 4.354

7.  Challenges in the Conversion of Manual Processes to Machine-Assisted Syntheses: Activation of Thioglycoside Donors with Aryl(trifluoroethyl)iodonium Triflimide.

Authors:  Regis C Saliba; Zachary J Wooke; Gabriel A Nieves; An-Hsiang Adam Chu; Clay S Bennett; Nicola L B Pohl
Journal:  Org Lett       Date:  2018-01-16       Impact factor: 6.005

8.  Toward Generalization of Iterative Small Molecule Synthesis.

Authors:  Jonathan W Lehmann; Daniel J Blair; Martin D Burke
Journal:  Nat Rev Chem       Date:  2018-03-07       Impact factor: 34.035

9.  The development of a dedicated polymer support for the solid-phase oligosaccharide synthesis.

Authors:  Matteo Panza; Dharmendra Neupane; Keith J Stine; Alexei V Demchenko
Journal:  Chem Commun (Camb)       Date:  2020-08-12       Impact factor: 6.222

Review 10.  Enzymatic Synthesis of Glycans and Glycoconjugates.

Authors:  Thomas Rexer; Dominic Laaf; Johannes Gottschalk; Hannes Frohnmeyer; Erdmann Rapp; Lothar Elling
Journal:  Adv Biochem Eng Biotechnol       Date:  2021       Impact factor: 2.635

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