63593-01-1Relevant articles and documents
Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose
Arzel, Laurence,Dubreuil, Didier,Dénès, Fabrice,Silvestre, Virginie,Mathé-Allainmat, Monique,Lebreton, Jacques
, p. 10742 - 10758 (2016/11/29)
An original and efficient stereocontrolled synthesis of ribonucleosidic homo- and heterodimers has been achieved from inexpensive d-xylose. This successful strategy involved the sequential introduction of nucleobases, using two stereocontrolled N-glycosidation reactions, from a common two-furanoside amide-linked scaffold offering the possibility of obtaining any given base sequence. The pertinence of this approach is illustrated through the preparation of the homodimers UU-34 and TT-35 in 18 steps with an excellent overall yield of more than 10% from d-xylose, while the heterodimer route led to UT-39 in 19 steps with around 10% overall yield.
Synthesis and application of a 5′-aldehyde phosphoramidite for covalent attachment of DNA to biomolecules
Miduturu, Chandrasekhar V.,Silverman, Scott K.
, p. 5774 - 5777 (2007/10/03)
We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5′-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5′-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5′-aldehyde-DNA with 2′-amino-2′-deoxy-RNA. These procedures should be generally applicable for attaching DNA to biomolecules.
