Neoglycosylation and neoglycorandomization: Enabling tools for the discovery of novel glycosylated bioactive probes and early stage leads - PubMed (original) (raw)

Neoglycosylation and neoglycorandomization: Enabling tools for the discovery of novel glycosylated bioactive probes and early stage leads

Randal D Goff et al. Medchemcomm. 2014.

Abstract

This review focuses upon the development, scope, and utility of the highly versatile chemoselective alkoxyamine-based 'neoglycosylation' reaction first described by Peri and Dumy. The fundamentals of neoglycosylation and the subsequent development of a 'neoglycorandomization' platform to afford differentially-glycosylated libraries of plant-based natural products, microbial-based natural products, and small molecule-based drugs for drug discovery applications are discussed.

PubMed Disclaimer

Conflict of interest statement

The authors report the following competing conflict of interest: J.S.T is a cofounder of Centrose (Madison, WI).

Figures

Figure 1

Figure 1

Neolgycosides by Peri and coworkers.,,,

Figure 2

Figure 2

Neoglycosides by Carrasco and André-Miral.–

Scheme 1

Scheme 1

Comparison of conventional glycosylation strategy (A) to neoglycosylation (B)

Scheme 2

Scheme 2

Chemoselective glycosylation between aminooxy-coupled compounds and aldehyde-containing sugars. (A) Anomeric-coupled glycopeptides reported by Mutter; (B) C6-coupled glycopeptides reported by Bertozzi.

Scheme 3

Scheme 3

Mechanism of the neoglycosylation reaction involving reducing sugars and alkoxyamines (R1NHOR2).

Scheme 4

Scheme 4

Typical methoxyamine handle installation on an aglycon.

Similar articles

Cited by

References

    1. Lin C-I, McCarty RM, Liu H-w. Chem Soc Rev. 2013;42:4377–4407. - PMC - PubMed
    1. Gantt RW, Peltier-Pain P, Thorson JS. Nat Prod Rep. 2011;28:1811–1853. - PubMed
    1. Singh S, Phillips GN, Jr, Thorson JS. Nat Prod Rep. 2012;29:1201–1237. - PMC - PubMed
    1. Hudak JE, Bertozzi CR. Chem Biol. 2014;21:16–37. - PMC - PubMed
    1. de Paz JL, Seeberger PH. Methods Mol Biol. 2012;808:1–12. - PubMed

Grants and funding

LinkOut - more resources