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Synthesis 2018; 50(04): 831-845
DOI: 10.1055/s-0036-1591082
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© Georg Thieme Verlag Stuttgart · New York

Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation

José J. Reina
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidad de Santiago de Compostela, Campus Vida, Rúa de Jenaro de la Fuente, s/n, 15782 Santiago de Compostela, La Coruña, Spain   Email: javier.montenegro@usc.es
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Alicia Rioboo
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidad de Santiago de Compostela, Campus Vida, Rúa de Jenaro de la Fuente, s/n, 15782 Santiago de Compostela, La Coruña, Spain   Email: javier.montenegro@usc.es
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Javier Montenegro  *
Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidad de Santiago de Compostela, Campus Vida, Rúa de Jenaro de la Fuente, s/n, 15782 Santiago de Compostela, La Coruña, Spain   Email: javier.montenegro@usc.es
› Author AffiliationsThis work was partially supported by the Spanish Agencia Estatal de Investigación (AEI) [CTQ2014–59646-R], the Xunta de Galicia (ED431G/09, ED431C 2017/25 and 2016-AD031) and the ERDF. J.M. received a Ramón y Cajal (RYC-2013–13784), an ERC-Stg (DYNAP- 677786) and a Young Investigator Grant from the Human Frontier Science Research Program (RGY0066/2017).
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Publication History

Received: 19 October 2017

Accepted after revision: 05 December 2017

Publication Date:
02 January 2018 (online)

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Published as part of the Bürgenstock Special Section 2017 Future Stars in Organic Chemistry

Abstract

The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycosyl aldehydes constitute a simple and accessible alternative to avoid loss of chiral information when conjugating, by oxime (or hydrazone) bonds, the aldehyde functionality present at the reducing end of natural carbohydrates.

Key words

neoglycoconjugates - glycosyl aldehydes - oxime bond formation - carbohydrates - bioorthogonal chemistry - chemoselective ligation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591082.
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