Automated, Multistep Continuous‐Flow Synthesis of 2,6‐Dideoxy and 3‐Amino‐2,3,6‐trideoxy Monosaccharide Building Blocks DOI
Subbarao Yalamanchili, Tu-Anh V. Nguyen,

Alexander Zsikla

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 133(43), P. 23355 - 23359

Published: Aug. 31, 2021

Abstract An automated continuous flow system capable of producing protected deoxy‐sugar donors from commercial material is described. Four 2,6‐dideoxy and two 3‐amino‐2,3,6‐trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields 74–131.5 minutes total reaction time. Several the reactions able to be concatenated into a process, avoiding need for chromatographic purification intermediates. The modular nature experimental setup allowed streams split different lines parallel synthesis multiple donors. Further, processes fully described through design an open‐source Python‐controlled automation platform.

Language: Английский

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions DOI
Chun‐Wei Chang, Mei‐Huei Lin, Chieh‐Kai Chan

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(22), P. 12413 - 12423

Published: Feb. 26, 2021

Abstract The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity hydroxyl groups influenced by steric, electronic structural effects, providing connection between experiments computer algorithms. subtle reactivity differences among on various carbohydrate molecules can be defined Aka, which is easily accessible simple convenient automation system assure high reproducibility accuracy. A diverse range donors acceptors with well‐defined promoters were organized processed designed software program “GlycoComputer” for prediction without involving sophisticated computational processing. importance Aka was further verified random forest algorithm, applicability tested synthesis Lewis skeleton show that accurately estimated.

Language: Английский

Citations

65

Tools for mammalian glycoscience research DOI Creative Commons
Matthew E. Griffin, Linda C. Hsieh‐Wilson

Cell, Journal Year: 2022, Volume and Issue: 185(15), P. 2657 - 2677

Published: July 1, 2022

Language: Английский

Citations

45

Automated, Multistep Continuous‐Flow Synthesis of 2,6‐Dideoxy and 3‐Amino‐2,3,6‐trideoxy Monosaccharide Building Blocks DOI
Subbarao Yalamanchili, Tu-Anh V. Nguyen,

Alexander Zsikla

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(43), P. 23171 - 23175

Published: Aug. 31, 2021

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11-32 % overall yields 74-131.5 minutes total reaction time. Several the reactions able to be concatenated into a process, avoiding need for chromatographic purification intermediates. The modular nature experimental setup allowed streams split different lines parallel synthesis multiple donors. Further, processes fully described through design an open-source Python-controlled automation platform.

Language: Английский

Citations

30

Progress and challenges in the synthesis of sequence controlled polysaccharides DOI Creative Commons
Giulio Fittolani, Theodore Tyrikos‐Ergas, Denisa Vargová

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 17, P. 1981 - 2025

Published: Aug. 5, 2021

The sequence, length and substitution of a polysaccharide influence its physical biological properties. Thus, sequence controlled polysaccharides are important targets to establish structure-properties correlations. Polymerization techniques enzymatic methods have been optimized obtain samples with well-defined patterns narrow molecular weight distribution. Chemical synthesis has granted access full control over the length. Here, we review progress towards polysaccharides. For each class polysaccharides, discuss available synthetic approaches their current limitations.

Language: Английский

Citations

28

HPLC‐Based Automated Synthesis and Purification of Carbohydrates DOI
Gustavo A. Kashiwagi, Laura Petrosilli, Samira Escopy

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: April 30, 2024

Reported herein is a new HPLC-based automated synthesizer (HPLC-A) capable of temperature-controlled synthesis and purification carbohydrates. The developed platform allows to perform various protecting group manipulations as well the O- N-glycosides. A fully was showcased in application different carbohydrate derivatives including glycosides, oligosaccharides, glycopeptides, glycolipids, nucleosides.

Language: Английский

Citations

4

Automated solid phase assisted synthesis of a heparan sulfate disaccharide library DOI
Sherif Ramadan, Guowei Su,

Kedar N. Baryal

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(11), P. 2910 - 2920

Published: Jan. 1, 2022

An automated machine-aided solid phase synthesis of heparan sulfate (HS) has been established for the first time. With significantly reduced number synthetic and purification steps, 16 HS disaccharides have readily assembled.

Language: Английский

Citations

16

Recent advances in the synthesis of extensive libraries of heparan sulfate oligosaccharides for structure–activity relationship studies DOI
Sherif Ramadan,

Morgan Mayieka,

Nicola L. B. Pohl

et al.

Current Opinion in Chemical Biology, Journal Year: 2024, Volume and Issue: 80, P. 102455 - 102455

Published: April 17, 2024

Language: Английский

Citations

2

HPLC‐Based Automated Synthesis of Glycans in Solution DOI
Samira Escopy, Yashapal Singh, Keith J. Stine

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(39)

Published: May 6, 2022

Abstract As the 21 st century unfolds with rapid changes, new challenges in research and development emerge. These prompted us to repurpose our HPLC−A platform that was previously used solid phase glycan synthesis a solution batch described herein. The modular character of HPLC allows for implementing attachments. To enable sequential multiple oligosaccharides single press button, we supplemented system four‐way split valve an automated fraction collector. This enabled operator load all reagents reactants autosampler, button start repetitive automation sequence, leave lab, upon return find products reactions ready purification, analysis, subsequent application.

Language: Английский

Citations

10

Automated Chemical Solid‐Phase Synthesis of Glycans DOI
Xiaona Li, You Yang

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(14), P. 1714 - 1728

Published: April 26, 2022

Abstract Automated chemical solid‐phase synthesis is an automation platform for rapid and reliable of glycans. Since the seminal work Glycan Assembly (AGA) disclosed by Seeberger in 2001, AGA has evolved from a proof‐of‐concept to robust technology streamlined production various types Through more than 20 years unceasing efforts, major breakthroughs including linkers, approved building blocks, synthesizers have been acquired, numerous influential achievements made complex glycan synthesis. In addition, HPLC‐assisted automated emerges as promising access this review, we highlight key advances field synthesis, especially AGA. The representative glycans based on also described.

Language: Английский

Citations

9

Chemical Synthesis of Human Milk Oligosaccharides: para‐Lacto‐N‐hexaose and para‐Lacto‐N‐neohexaose DOI Open Access
Yashapal Singh, Samira Escopy, Melanie Shadrick

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(64)

Published: Aug. 28, 2023

Abstract Human milk oligosaccharides (HMO) have emerged as a very active area of research in glycoscience and nutrition. HMO are involved the early development infants may help to prevent certain diseases. The chemical methods for obtaining individual aids global effort dedicated understanding roles these biomolecules. Reported herein is synthesis two common core hexasaccharides found human milk, i. e. para ‐lacto‐ N ‐hexaose ( p LNH) ‐neohexaose LNnH). After screening multiple leaving groups temporary protecting group combinations, 3+3 convergent coupling strategy was work best linear glycans.

Language: Английский

Citations

5