A Convenient Method for the Preparation of Hapten Phosphoramidites
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in Bioconjugate Chemistry
- Vol. 7 (2) , 274-280
- https://doi.org/10.1021/bc960004m
Abstract
Automated incorporation of haptens at the 3‘ or 5‘ end of oligonucleotides required the preparation of the corresponding hapten phosphoramidites. The requisite 1,3-diol framework was prepared in two steps from a carboxylic acid precursor first by a two-carbon homologation using Meldrum's acid to form the corresponding 3-oxo ester and then subsequent reduction to the diol. The primary alcohol was protected with a dimethoxytrityl group, while the secondary alcohol was converted to the reactive phosphoramidite.Keywords
This publication has 6 references indexed in Scilit:
- Synthesis of novel phosphoramidite derivatives bearing pyrenyl and dansyl groupsTetrahedron Letters, 1995
- Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotidesBioconjugate Chemistry, 1991
- A universal solid support for the synthesis of 3′-thiol group containing oligonucleotidesTetrahedron Letters, 1990
- Synthesis of oligonucleotides containing a carboxyl group at either their 5′ end or their 3′ end and their subsequent derivatization by an intercalating agentTetrahedron Letters, 1990
- Solid-phase synthesis of modified oligodeoxyribonucleotides with an acridine derivative or a thiophosphate group at their 3′endTetrahedron Letters, 1989
- Meldrum's acid in organic synthesis. 2. A general and versatile synthesis of .beta.-keto estersThe Journal of Organic Chemistry, 1978