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Uronic Acids in Oligosaccharide and Glycoconjugate Synthesis

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Reactivity Tuning in Oligosaccharide Assembly

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 301))

Abstract

This chapter describes the assembly of uronic acid containing oligosaccharides and glycoconjugates. Two strategies are available to access these target molecules, namely a pre-glycosylation oxidation approach, in which uronic acid building blocks are used, and a post-glycosylation oxidation strategy, which employs an oxidation step after the assembly of the oligosaccharide chain. Because uronic acid building blocks are generally considered to be less reactive than their non-oxidized counterparts, the latter approach has found most application in carbohydrate synthesis. With the aid of selected examples of recent syntheses of biologically relevant oligosaccharides and glycoconjugates, the reactivity of different uronic acid building blocks is evaluated. From these examples it is apparent that the generally assumed low reactivity of uronic acids does not a priori rule out an efficient assembly of these target compounds. Besides influencing the reactivity of a given pyranoside, the C-5 carboxylic acid function can also have a profound effect on the stereochemical course of a glycosylation reaction, which can be exploited in the stereoselective formation of glycosidic bonds.

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Notes

  1. 1.

    This work is currently in progress in our laboratory.

  2. 2.

    We have postulated that the unusually high α-selectivity observed for condensations of gulosyl donors originates from the α-selective axial attack of the gulosyl 3H4-cation. See [102].

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Authors and Affiliations

  1. Leiden Institute of Chemistry, Leiden University, 9502, 2300 RA, Leiden, The Netherlands

    Jeroen D. C. Codée, Alphert E. Christina, Marthe T. C. Walvoort, Herman S. Overkleeft & Gijsbert A. van der Marel

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  1. Jeroen D. C. Codée
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  2. Alphert E. Christina
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  4. Herman S. Overkleeft
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  5. Gijsbert A. van der Marel
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Correspondence to Jeroen D. C. Codée or Gijsbert A. van der Marel .

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  1. Natural Products and Glycotechnology Res, Swarthmore Road 4118, Durham, 27706, North Carolina, USA

    Bert Fraser-Reid

  2. Instituto de Quimica Orgánica General (C, Juan de la Cierva 3, Madrid, 28006, Spain

    J. Cristóbal López

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Codée, J.D.C., Christina, A.E., Walvoort, M.T.C., Overkleeft, H.S., van der Marel, G.A. (2010). Uronic Acids in Oligosaccharide and Glycoconjugate Synthesis. In: Fraser-Reid, B., Cristóbal López, J. (eds) Reactivity Tuning in Oligosaccharide Assembly. Topics in Current Chemistry, vol 301. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_111

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