Fluorous-Tag-Assisted Synthesis of GAG-Like Oligosaccharides.

Chromatography Glycosaminoglycans / chemistry Glycosylation Oligosaccharides Solid Phase Extraction
Fluorous solid-phase extraction Fluorous tag Glycosaminoglycans Glycosylation Oligosaccharide synthesis

Journal

Methods in molecular biology (Clifton, N.J.)
ISSN: 1940-6029
Titre abrégé: Methods Mol Biol
Pays: United States
ID NLM: 9214969

Informations de publication

Date de publication:
2022
Historique:
entrez: 9 10 2021
pubmed: 10 10 2021
medline: 8 1 2022
Statut: ppublish

Résumé

The classic, solution-phase synthesis of glycosaminoglycan (GAG) oligosaccharides is hampered by the numerous, time-consuming chromatographic purifications required for the isolation of the glycosylation products after each coupling step between sugar building blocks. Here, we present a detailed experimental procedure for a glycosylation reaction involving a glycosyl acceptor unit that is equipped with a perfluorinated tag. The presence of this fluorous tail allows the quick purification of the desired glycosylation product by performing a simple fluorous solid-phase extraction (F-SPE). The described fluorous-tag-assisted glycosylation strategy greatly facilitates the assembly of building blocks, speeding up the preparation of biologically relevant GAG-like oligomers.

Identifiants

DOI: 10.1007/978-1-0716-1398-6_4 PMID: 34626368
pubmed: 34626368
doi: 10.1007/978-1-0716-1398-6_4
doi:

Substances chimiques

Glycosaminoglycans 0
Oligosaccharides 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

37-47

Informations de copyright

© 2022. Springer Science+Business Media, LLC, part of Springer Nature.

Références

Mende M, Bednarek C, Wawryszyn M, Sauter P, Biskup MB, Schepers U, Braese S (2016) Chemical synthesis of glycosaminoglycans. Chem Rev 116(14):8193–8255. https://doi.org/10.1021/acs.chemrev.6b00010
doi: 10.1021/acs.chemrev.6b00010 pubmed: 27410264
Panza M, Pistorio SG, Stine KJ, Demchenko AV (2018) Automated chemical oligosaccharide synthesis: novel approach to traditional challenges. Chem Rev 118(17):8105–8150. https://doi.org/10.1021/acs.chemrev.8b00051
doi: 10.1021/acs.chemrev.8b00051 pubmed: 29953217 pmcid: 6522228
Walvoort MTC, Volbeda AG, Reintjens NRM, van den Elst H, Plante OJ, Overkleeft HS, van der Marel GA, Codee JDC (2012) Automated solid-phase synthesis of hyaluronan oligosaccharides. Org Lett 14(14):3776–3779. https://doi.org/10.1021/ol301666n
doi: 10.1021/ol301666n pubmed: 22780913
de Jong AR, Volbeda AG, Hagen B, van den Elst H, Overkleeft HS, van der Marel GA, Codee JDC (2013) A second-generation tandem ring-closing metathesis cleavable linker for solid-phase oligosaccharide synthesis. Eur J Org Chem 2013(29):6644–6655. https://doi.org/10.1002/ejoc.201301055
doi: 10.1002/ejoc.201301055
Eller S, Collot M, Yin J, Hahm HS, Seeberger PH (2013) Automated solid-phase synthesis of chondroitin sulfate glycosaminoglycans. Angew Chem Int Ed 52(22):5858–5861. https://doi.org/10.1002/anie.201210132
doi: 10.1002/anie.201210132
Kandasamy J, Schuhmacher F, Hahm HS, Kleina JC, Seeberger PH (2014) Modular automated solid phase synthesis of dermatan sulfate oligosaccharides. Chem Commun 50(15):1875–1877. https://doi.org/10.1039/c3cc48860h
doi: 10.1039/c3cc48860h
Hahm HS, Broecker F, Kawasaki F, Mietzsch M, Heilbronn R, Fukuda M, Seeberger PH (2017) Automated glycan assembly of oligo-N-acetyllactosamine and keratan sulfate probes to study virus-glycan interactions. Chem 2(1):114–124. https://doi.org/10.1016/j.chempr.2016.12.004
doi: 10.1016/j.chempr.2016.12.004
Kulkarni SS, Wang C-C, Sabbavarapu NM, Podilapu AR, Liao P-H, Hung S-C (2018) “One-Pot” protection, glycosylation, and protection-glycosylation strategies of carbohydrates. Chem Rev 118(17):8025–8104. https://doi.org/10.1021/acs.chemrev.8b00036
doi: 10.1021/acs.chemrev.8b00036 pubmed: 29870239
Jaipuri FA, Pohl NL (2008) Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers. Org Biomol Chem 6(15):2686–2691. https://doi.org/10.1039/b803451f
doi: 10.1039/b803451f pubmed: 18633525
Tang SL, Pohl NLB (2015) Automated solution-phase synthesis of beta-1,4-mannuronate and beta-1,4-mannan. Org Lett 17(11):2642–2645. https://doi.org/10.1021/acs.orglett.5b01013
doi: 10.1021/acs.orglett.5b01013 pubmed: 25955886 pmcid: 4460921
Zhang W, Curran DP (2006) Synthetic applications of fluorous solid-phase extraction (F-SPE). Tetrahedron 62(51):11837–11865. https://doi.org/10.1016/j.tet.2006.08.051
doi: 10.1016/j.tet.2006.08.051 pubmed: 18509513 pmcid: 2396515
Bhaduri S, Pohl NLB (2016) Fluorous-tag assisted syntheses of sulfated keratan sulfate oligosaccharide fragments. Org Lett 18(6):1414–1417. https://doi.org/10.1021/acs.orglett.6b00344
doi: 10.1021/acs.orglett.6b00344 pubmed: 26958998
Cai C, Dickinson DM, Li L, Masuko S, Suflita M, Schultz V, Nelson SD, Bhaskar U, Liu J, Linhardt RJ (2014) Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides. Org Lett 16(8):2240–2243. https://doi.org/10.1021/ol500738g
doi: 10.1021/ol500738g pubmed: 24697306 pmcid: 3998769
Zong C, Venot A, Dhamale O, Boons G-J (2013) Fluorous supported modular synthesis of heparan sulfate oligosaccharides. Org Lett 15(2):342–345. https://doi.org/10.1021/ol303270v
doi: 10.1021/ol303270v pubmed: 23293947 pmcid: 3563243
Mena-Barragan T, de Paz JL, Nieto PM (2019) Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides. Beilstein J Org Chem 15:137–144. https://doi.org/10.3762/bjoc.15.14
doi: 10.3762/bjoc.15.14 pubmed: 30745989 pmcid: 6350880
Macchione G, de Paz JL, Nieto PM (2014) Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach. Carbohydr Res 394:17–25. https://doi.org/10.1016/j.carres.2014.05.007
doi: 10.1016/j.carres.2014.05.007 pubmed: 24930061
Ko KS, Jaipuri FA, Pohl NL (2005) Fluorous-based carbohydrate microarrays. J Am Chem Soc 127(38):13162–13163. https://doi.org/10.1021/ja054811k
doi: 10.1021/ja054811k pubmed: 16173741
Maza S, de Paz JL, Nieto PM (2019) Synthesis of a fluorous-tagged hexasaccharide and interaction with growth factors using sugar-coated microplates. Molecules 24(8). https://doi.org/10.3390/molecules24081591
Maza S, Gandia-Aguado N, de Paz JL, Nieto PM (2018) Fluorous-tag assisted synthesis of a glycosaminoglycan mimetic tetrasaccharide as a high-affinity FGF-2 and midkine ligand. Bioorg Med Chem 26(5):1076–1085. https://doi.org/10.1016/j.bmc.2018.01.022
doi: 10.1016/j.bmc.2018.01.022 pubmed: 29409708

Auteurs

José L de Paz (JL)

Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), cicCartuja, CSIC and Universidad de Sevilla, Sevilla, Spain. jlpaz@iiq.csic.es.

Pedro M Nieto (PM)

Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), cicCartuja, CSIC and Universidad de Sevilla, Sevilla, Spain. pedro.nieto@iiq.csic.es.

Articles similaires

Post-translational modifications of fibrinogen: implications for clotting, fibrin structure and degradation.

Francesca Nencini, Alessandra Bettiol, Flavia Rita Argento et al.
1.00
Protein Processing, Post-Translational Humans Blood Coagulation Fibrin Fibrinogen

The post-translational modification O-GlcNAc is a sensor and regulator of metabolism.

Murielle M Morales, Matthew R Pratt
1.00
Protein Processing, Post-Translational Humans Acetylglucosamine Animals Neoplasms

Protein O-GlcNAcylation coupled to Hippo signaling drives vascular dysfunction in diabetic retinopathy.

Yi Lei, Qiangyun Liu, Binggui Chen et al.
1.00
Diabetic Retinopathy Animals Humans Signal Transduction Protein Serine-Threonine Kinases

Positions of cysteine residues reveal local clusters and hidden relationships to Sequons and Transmembrane domains in Human proteins.

Manthan Desai, Bingyun Sun
1.00
Humans Cysteine Membrane Proteins Protein Domains Glycosylation

Classifications MeSH

questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Chromatographie › Fluorous-Tag-Assisted Synthesis of GAG-Like...
questionsmedicales.fr › Glucides › Polyosides › Glycosaminoglycanes › Fluorous-Tag-Assisted Synthesis of GAG-Like...
questionsmedicales.fr › Métabolisme › Métabolisme glucidique › Glycosylation › Fluorous-Tag-Assisted Synthesis of GAG-Like...
questionsmedicales.fr › Glucides › Polyosides › Oligosaccharides › Fluorous-Tag-Assisted Synthesis of GAG-Like...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Fractionnement chimique › Extraction en phase solide › Fluorous-Tag-Assisted Synthesis of GAG-Like...