Microwave-Assisted Automated Glycan Assembly

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2021 Jun 1

PMID 34060822

Citations 9

Authors

Jose Danglad-Flores

Sabrina Leichnitz

Eric T Sletten

A Abragam Joseph

Klaus Bienert

Kim Le Mai Hoang

Peter H Seeberger

Affiliations

Soon will be listed here.

Abstract

Automated synthesis of DNA, RNA, and peptides provides quickly and reliably important tools for biomedical research. Automated glycan assembly (AGA) is significantly more challenging, as highly branched carbohydrates require strict regio- and stereocontrol during synthesis. A new AGA synthesizer enables rapid temperature adjustment from -40 to +100 °C to control glycosylations at low temperature and accelerates capping, protecting group removal, and glycan modifications using elevated temperatures. Thereby, the temporary protecting group portfolio is extended from two to four orthogonal groups that give rise to oligosaccharides with up to four branches. In addition, sulfated glycans and unprotected glycans can be prepared. The new design reduces the typical coupling cycles from 100 to 60 min while expanding the range of accessible glycans. The instrument drastically shortens and generalizes the synthesis of carbohydrates for use in biomedical and material science.

Citing Articles

Automated Synthesis of Algal Fucoidan Oligosaccharides.

Crawford C, Schultz-Johansen M, Luong P, Vidal-Melgosa S, Hehemann J, Seeberger P J Am Chem Soc. 2024; 146(27):18320-18330.

PMID: 38916244 PMC: 11240576. DOI: 10.1021/jacs.4c02348.

Synthesis of a heparan sulfate tetrasaccharide using automated glycan assembly.

Pongener I, Sletten E, Danglad-Flores J, Seeberger P, Miller G Org Biomol Chem. 2024; 22(7):1395-1399.

PMID: 38291974 PMC: 10865181. DOI: 10.1039/d3ob01909h.

Linker, loading, and reaction scale influence automated glycan assembly.

Dal Colle M, Ricardo M, Hribernik N, Danglad-Flores J, Seeberger P, Delbianco M Beilstein J Org Chem. 2023; 19:1015-1020.

PMID: 37440787 PMC: 10334207. DOI: 10.3762/bjoc.19.77.

VaporSPOT: Parallel Synthesis of Oligosaccharides on Membranes.

Tsouka A, Dallabernardina P, Mende M, Sletten E, Leichnitz S, Bienert K J Am Chem Soc. 2022; 144(43):19832-19837.

PMID: 36269942 PMC: 9634802. DOI: 10.1021/jacs.2c07285.

Semisynthetic Glycoconjugate Vaccine Candidates against O25B Induce Functional IgG Antibodies in Mice.

Naini A, Bartetzko M, Sanapala S, Broecker F, Wirtz V, Lisboa M JACS Au. 2022; 2(9):2135-2151.

PMID: 36186572 PMC: 9516715. DOI: 10.1021/jacsau.2c00401.

References

Caruthers M . Gene synthesis machines: DNA chemistry and its uses. Science. 1985; 230(4723):281-5. DOI: 10.1126/science.3863253. View

Abragam Joseph A, Pardo-Vargas A, Seeberger P . Total Synthesis of Polysaccharides by Automated Glycan Assembly. J Am Chem Soc. 2020; 142(19):8561-8564. PMC: 7304863. DOI: 10.1021/jacs.0c00751. View

Compostella F, Ronchi S, Panza L, Mariotti S, Mori L, De Libero G . Synthesis of sulfated galactocerebrosides from an orthogonal beta-D-galactosylceramide scaffold for the study of CD1-antigen interactions. Chemistry. 2006; 12(21):5587-95. DOI: 10.1002/chem.200501586. View

MERRIFIELD R . Automated synthesis of peptides. Science. 1965; 150(3693):178-85. DOI: 10.1126/science.150.3693.178. View

Yu Y, Kononov A, Delbianco M, Seeberger P . A Capping Step During Automated Glycan Assembly Enables Access to Complex Glycans in High Yield. Chemistry. 2018; 24(23):6075-6078. DOI: 10.1002/chem.201801023. View

Schmidt D, Schuhmacher F, Geissner A, Seeberger P, Pfrengle F . Automated synthesis of arabinoxylan-oligosaccharides enables characterization of antibodies that recognize plant cell wall glycans. Chemistry. 2015; 21(15):5709-13. DOI: 10.1002/chem.201500065. View

Lin S, Lowary T . Synthesis of a Highly Branched Nonasaccharide Chlorella Virus -Glycan Using a "Counterclockwise" Assembly Approach. Org Lett. 2020; 22(19):7645-7649. DOI: 10.1021/acs.orglett.0c02839. View

Angelone D, Hammer A, Rohrbach S, Krambeck S, Granda J, Wolf J . Convergence of multiple synthetic paradigms in a universally programmable chemical synthesis machine. Nat Chem. 2020; 13(1):63-69. DOI: 10.1038/s41557-020-00596-9. View

Guberman M, Seeberger P . Automated Glycan Assembly: A Perspective. J Am Chem Soc. 2019; 141(14):5581-5592. PMC: 6727384. DOI: 10.1021/jacs.9b00638. View

10.

Xu Z, Li H, Li W, Cao G, Zhang Q, Li K . Large-scale production of graphene by microwave synthesis and rapid cooling. Chem Commun (Camb). 2010; 47(4):1166-8. DOI: 10.1039/c0cc03520c. View

11.

Thota V, Ferguson M, Sweeney R, Lowary T . Synthesis of the Campylobacter jejuni 81-176 Strain Capsular Polysaccharide Repeating Unit Reveals the Absolute Configuration of its O-Methyl Phosphoramidate Motif. Angew Chem Int Ed Engl. 2018; 57(47):15592-15596. DOI: 10.1002/anie.201810222. View

12.

Nielsen M, Pedersen C . Catalytic Glycosylations in Oligosaccharide Synthesis. Chem Rev. 2018; 118(17):8285-8358. DOI: 10.1021/acs.chemrev.8b00144. View

13.

Guberman M, Brautigam M, Seeberger P . Automated glycan assembly of Lewis type I and II oligosaccharide antigens. Chem Sci. 2019; 10(21):5634-5640. PMC: 6552968. DOI: 10.1039/c9sc00768g. View

14.

Pan X, Lathwal S, Mack S, Yan J, Das S, Matyjaszewski K . Automated Synthesis of Well-Defined Polymers and Biohybrids by Atom Transfer Radical Polymerization Using a DNA Synthesizer. Angew Chem Int Ed Engl. 2017; 56(10):2740-2743. PMC: 5341381. DOI: 10.1002/anie.201611567. View

15.

Zhai C, Teng N, Pan B, Chen J, Liu F, Zhu J . Revealing the importance of non-thermal effect to strengthen hydrolysis of cellulose by synchronous cooling assisted microwave driving. Carbohydr Polym. 2018; 197:414-421. DOI: 10.1016/j.carbpol.2018.06.031. View

16.

Manlusoc J, Hsieh C, Hsieh C, Salac E, Lee Y, Tsai P . Pharmacologic Application Potentials of Sulfated Polysaccharide from Marine Algae. Polymers (Basel). 2019; 11(7). PMC: 6680640. DOI: 10.3390/polym11071163. View

17.

Pardo-Vargas A, Delbianco M, Seeberger P . Automated glycan assembly as an enabling technology. Curr Opin Chem Biol. 2018; 46:48-55. DOI: 10.1016/j.cbpa.2018.04.007. View

18.

Kappe C, Pieber B, Dallinger D . Microwave effects in organic synthesis: myth or reality?. Angew Chem Int Ed Engl. 2012; 52(4):1088-94. DOI: 10.1002/anie.201204103. View

19.

Hahm H, Schlegel M, Hurevich M, Eller S, Schuhmacher F, Hofmann J . Automated glycan assembly using the Glyconeer 2.1 synthesizer. Proc Natl Acad Sci U S A. 2017; 114(17):E3385-E3389. PMC: 5410834. DOI: 10.1073/pnas.1700141114. View

20.

Volbeda A, Kistemaker H, Overkleeft H, van der Marel G, Filippov D, Codee J . Chemoselective Cleavage of p-Methoxybenzyl and 2-Naphthylmethyl Ethers Using a Catalytic Amount of HCl in Hexafluoro-2-propanol. J Org Chem. 2015; 80(17):8796-806. DOI: 10.1021/acs.joc.5b01030. View