Synthesis of Mannose and Galactose Oligonucleotide Conjugates by Bi-click chemistry

Abstract

Glyco oligonucleotide conjugates, each exhibiting two mannose and two galactose residues, were efficiently synthesized by two successive 1,3-dipolar cycloadditions (click chemistry). Two phosphoramidite derivatives were used: one bearing a bromoalkyl group as a precursor to azide functionalization and another bearing a propargyl group. After a first cycloaddition with a mannosyl-azide derivative, the bromine atoms were substituted with NaN(3) and a second click reaction was performed with a 1'-O-propargyl galactose, affording the heteroglyco oligonucleotide conjugate.

On the Compatibility of Azides in Phosphoramidite‐Based Couplings: Synthesis of a Novel, Convertible Azido‐Functionalized CyPLOS Analogue

“…[16,19] Alternatively, 5Ј-azido-oligonucleotides were prepared through 5Ј-iodination, [13] or by use of bromoalkyl building blocks. The latter were inserted into an oligonucleotide sequence [21] or at the 5Ј-end, [15,17] by using an automated solid-phase synthesis protocol. Both synthetic ways were followed by treatment with sodium azide.…”

DNA Three Way Junction Core Decorated with Amino Acids-Like Residues-Synthesis and Characterization

“…and sodium ascorbate (2 eq.) at 60 • C for 0.5 to 1.5 h [29,30]. His S 3 was obtained after desalting and Ser S 2 was recovered after concentrated ammonia/aqueous methylamine (AMA) treatment for pivaloyl protective group removal prior to purification on Sephadex G-25 columns.…”

Multivalency in heterogeneous glycoenvironments: hetero-glycoclusters, -glycopolymers and -glycoassemblies

“…4). Morvan and co-workers 34 have implemented the CuAAC ligation strategy to access glycooligonucleotide conjugates exhibiting two aMan and two bGal residues (31, Scheme 6) intended to be incorporated in novel heteroglycoarrays for lectin affinity investigation upon DNA-directed immobilization. The methodology involves the use of two functionalized phosphoramidite derivatives, one bearing a bromoalkyl group as precursor of azide and another one that bears a clickable propargyl group.…”