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Review
. 2018 Sep 12;118(17):8105-8150.
doi: 10.1021/acs.chemrev.8b00051. Epub 2018 Jun 28.

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Matteo Panza  1 , Salvatore G Pistorio  1 , Keith J Stine  1 , Alexei V Demchenko  1
Affiliations
Review

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Matteo Panza et al. Chem Rev. .

Abstract

Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Figure 1.
Figure 1.
Representative structures of common linear and branched oligosaccharide motifs.
Figure 2.
Figure 2.
Directing neighboring participating groups at C-2.
Figure 3.
Figure 3.
Solid supports for oligosaccharide synthesis: (A) Merrifield’s resin, (B) Tentagel, and (C) JandaJel.
Figure 4.
Figure 4.
Recently introduced linkers for polymer-supported oligosaccharide synthesis.
Figure 5.
Figure 5.
Split-valve setup for the alternate-pump system.
Figure 6.
Figure 6.
Representative 1,2-cis-linked oligosaccharides synthesized using Glyconeer 2.1
Scheme 1.
Scheme 1.
General Outline of the Chemical Glycosylation Reaction
Scheme 2.
Scheme 2.
Examples of Urea and Thiourea-Based Organocatalytic Reactions
Scheme 3.
Scheme 3.
Synthesis of β-Mannosides via Intramolecular Aglycone Delivery
Scheme 4.
Scheme 4.
Conventional Linear Oligosaccharide Synthesis with Alternating Glycosylation and Deprotection Steps
Scheme 5.
Scheme 5.
Convergent Block Synthesis of Ganglioside GP3
Scheme 6.
Scheme 6.
(A) Chemoselective and (B) Selective Activation Approaches to Expeditious Oligosaccharide Synthesis
Scheme 7.
Scheme 7.
Hexasaccharide Synthesis in Five Selective Activation Steps
Scheme 8.
Scheme 8.
Orthogonal Activation of Phenylthio Glycosides and Fluorides
Scheme 9.
Scheme 9.
Glycal-Epoxide Method for Iterative Oligosaccharide Synthesis
Scheme 10.
Scheme 10.
Two-Directional Approach for the Synthesis of Pentasaccharide 54
Scheme 11.
Scheme 11.
One-Pot Synthesis of Tetrasaccharide 59 via Chemoselective Activation
Scheme 12.
Scheme 12.
One-Pot Synthesis of Tetrasaccharide 62 via Sequential Selective Activation of Building Blocks Equipped with Different Leaving Groups
Scheme 13.
Scheme 13.
Preactivation-Based One-Pot Synthesis of Globo-H Hexasaccharide 67
Scheme 14.
Scheme 14.
Glycosylation on Polymer Support
Scheme 15.
Scheme 15.
Acceptor-Bound Approach to the Synthesis of Oligosaccharide 73
Scheme 16.
Scheme 16.
Chiral Auxiliary-Assisted Synthesis of 1,2-cis-Linked Oligosaccharide 79
Scheme 17.
Scheme 17.
Donor-Bound Synthesis of Pentasaccharide82
Scheme 18.
Scheme 18.
Orthogonal Synthesis of a Combinatorial Library on Solid Phase
Scheme 19.
Scheme 19.
Peptide-Templated Oligosaccharide Synthesis on Polymer Support
Scheme 20.
Scheme 20.
STICS: Surface-Tethered Iterative Carbohydrate Synthesis
Scheme 21.
Scheme 21.
Synthesis of Dimeric Lex Hexasaccharide Using Soluble Polymer Support
Scheme 22.
Scheme 22.
Fluorous Tag-Assisted Synthesis of Pentasaccharide 105
Scheme 23.
Scheme 23.
Convergent/Orthogonal Ionic Liquid-Tagged Synthesis of Mannans
Scheme 24.
Scheme 24.
Solution Phase Automation of the Oligosaccharide Synthesis in One Pot Using Parallel Synthesizer Quest 210a
Scheme 25.
Scheme 25.
Synthesis of Oligosaccharides 122a–122c Using a Modified Peptide Synthesizer
Scheme 26.
Scheme 26.
Automated Synthesis of Globo H Hexasaccharide
Scheme 27.
Scheme 27.
Automated Synthesis of β-Mannosides
Scheme 28.
Scheme 28.
Fluorous Tag Supported Synthesis of a Tetrasaccharide 322 in a Microreactor
Scheme 29.
Scheme 29.
Automated Synthesis of Pentamannose 140 Using Fluorous Supporta
Scheme 30.
Scheme 30.
Automated Synthesis of β-Mannuronan and β-Mannan
Scheme 31.
Scheme 31.
Automated Sequence to the Branched Oligomannan Fragment from N-Glycans
Scheme 32.
Scheme 32.
Automated Synthesis of N-Glycan Core Using the Dedicated Synthesizer
Scheme 33.
Scheme 33.
Automated Synthesis of Manno Triantamer 160
Scheme 34.
Scheme 34.
Automated Synthesis a 50-mer 162 Using Glyconeer 2.1a
Scheme 35.
Scheme 35.
Automation of the Sialylation Reaction
Scheme 36.
Scheme 36.
Automation of 1,2-cis Glycosylation
Scheme 37.
Scheme 37.
Automated Synthesis of β-Manno-Linked Dodecasaccharide 179
Scheme 38.
Scheme 38.
Synthesis of the Branched Hexasaccharide Composed of Multiple Arabinofuranosyl Residues
Scheme 39.
Scheme 39.
Synthesis of a Chondroitin Sulfate
Scheme 40.
Scheme 40.
Synthesis of Hyaluronic Acid Fragments
Scheme 41.
Scheme 41.
Glycopeptide Synthetic Sequence
Scheme 42.
Scheme 42.
Synthesis of a Representative Galactosylated Xyloglucan for Generating of Oligosaccharide Libraries
Scheme 43.
Scheme 43.
HPLC-Assisted Automated Oligosaccharide Synthesis
Scheme 44.
Scheme 44.
Use of an Autosampler As the Mode for Reagent Delivery for the HPLC-Based Automation
Scheme 45.
Scheme 45.
HPLC-Assisted Surface-Tethered Synthesis of Disaccharides 209
Scheme 46.
Scheme 46.
Automated Solution Phase Synthesis Using Electrochemical Activationa
Scheme 47.
Scheme 47.
Electrochemical Approach to GPI Anchor’S CoreTrisaccharide
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