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Literature DB >> 22646669

HPLC-assisted automated oligosaccharide synthesis.

N Vijaya Ganesh¹, Kohki Fujikawa, Yih Horng Tan, Keith J Stine, Alexei V Demchenko.

Abstract

A standard HPLC was adapted to polymer supported oligosaccharide synthesis. Solution-based reagents are delivered using a software-controlled solvent delivery system. The reaction progress and completion can be monitored in real time using a standard UV detector. All steps of oligosaccharide assembly including loading, glycosylation, deprotection, and cleavage can be performed using this setup.

Entities: Chemical Gene Species

Mesh：

Substances：
Oligosaccharides
Polymers

Year: 2012 PMID： 22646669 PMCID： PMC3426652 DOI： 10.1021/ol301105y

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

30 in total

1. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary-protecting-group pattern.

Authors: Xiangyang Wu; Matthias Grathwohl; Richard R Schmidt
Journal: Angew Chem Int Ed Engl Date: 2002-12-02 Impact factor: 15.336

Review 2. Development of an automated oligosaccharide synthesizer.

Authors: Obadiah J Plante; Emma R Palmacci; Peter H Seeberger
Journal: Adv Carbohydr Chem Biochem Date: 2003 Impact factor: 12.200

3. Development and application of a solution-phase automated synthesizer, 'ChemKonzert'.

Authors: Kazuhiro Machida; Yoichiro Hirose; Shinichiro Fuse; Tohru Sugawara; Takashi Takahashi
Journal: Chem Pharm Bull (Tokyo) Date: 2010-01 Impact factor: 1.645

4. 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

Review 5. Automated synthesis of oligosaccharides as a basis for drug discovery.

Authors: Peter H Seeberger; Daniel B Werz
Journal: Nat Rev Drug Discov Date: 2005-09 Impact factor: 84.694

Review 6. Ionic liquids in oligosaccharide synthesis: towards mucin-type glycan probes.

Authors: M Carmen Galan; Anthony P Corfield
Journal: Biochem Soc Trans Date: 2010-10 Impact factor: 5.407

7. Ionic catch and release oligosaccharide synthesis (ICROS).

Authors: Anh-Tuan Tran; Richard Burden; Daugirdas T Racys; M Carmen Galan
Journal: Chem Commun (Camb) Date: 2011-03-09 Impact factor: 6.222

8. Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched alpha-glucan.

Authors: Thomas J Boltje; Jin-Hwan Kim; Jin Park; Geert-Jan Boons
Journal: Nat Chem Date: 2010-05-23 Impact factor: 24.427

9. Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans.

Authors: S Rio; J M Beau; J C Jacquinet
Journal: Carbohydr Res Date: 1991-10-14 Impact factor: 2.104

10. From solution phase to "on-column" chemistry: trichloroacetimidate-based glycosylation promoted by perchloric acid-silica.

Authors: Balaram Mukhopadhyay; Sarah V Maurer; Nadine Rudolph; Renate M van Well; David A Russell; Robert A Field
Journal: J Org Chem Date: 2005-10-28 Impact factor: 4.354

28 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. Overcoming the limited availability of human milk oligosaccharides: challenges and opportunities for research and application.

Authors: Lars Bode; Nikhat Contractor; Daniela Barile; Nicola Pohl; Anthony R Prudden; Geert-Jan Boons; Yong-Su Jin; Stefan Jennewein
Journal: Nutr Rev Date: 2016-10 Impact factor: 7.110

3. Recent Liquid Chromatographic Approaches and Developments for the Separation and Purification of Carbohydrates.

Authors: Gabe Nagy; Tianyuan Peng; Nicola L B Pohl
Journal: Anal Methods Date: 2017-05-24 Impact factor: 2.896

4. Surface-tethered iterative carbohydrate synthesis: a spacer study.

Authors: N Vijaya Ganesh; Kohki Fujikawa; Yih Horng Tan; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal: J Org Chem Date: 2013-07-08 Impact factor: 4.354

5. Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives.

Authors: Mallory K Kern; Nicola L B Pohl
Journal: Org Lett Date: 2020-05-20 Impact factor: 6.005

6. HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery.

Authors: Salvatore G Pistorio; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal: J Org Chem Date: 2016-09-14 Impact factor: 4.354

Review 7. Designing sugar mimetics: non-natural pyranosides as innovative chemical tools.

Authors: Regis C Saliba; Nicola Lb Pohl
Journal: Curr Opin Chem Biol Date: 2016-09-10 Impact factor: 8.822

8. 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

9. Machine-Driven Enzymatic Oligosaccharide Synthesis by Using a Peptide Synthesizer.

Authors: Jiabin Zhang; Congcong Chen; Madhusudhan Reddy Gadi; Christopher Gibbons; Yuxi Guo; Xuefeng Cao; Garrett Edmunds; Shuaishuai Wang; Ding Liu; Jin Yu; Liuqing Wen; Peng G Wang
Journal: Angew Chem Int Ed Engl Date: 2018-11-26 Impact factor: 15.336

10. 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