The Phenylacetyl Group-The First Amino Protecting Group That Can Be Removed Enzymatically from Oligonucleotides in Solution and on a Solid Support

摘要

A central problem in the chemical synthesis of oligodeoxy-nucleotides on solid supports is the protection and deprotection of the amino groups of the different nueleobases. Even under the strongly basic conditions required for the removal of the established blocking groups deprotection may remain incomplete, and unwanted side reactions like the formation of 2,6-diaminopurines from 6-O-alkylated guunine moieties may occur. In addition, new protecting groups are needed, for example, for the construction of complex and sensitive nucle-opeptides, nonradioactive DNA probes, and amino-acyl-modified tRNAs and for the preparation of matrix-bound deprotected DNA fragments. Therefore, the development of new methods for the selective protection and deprotection of the amino functions of nucleobases under alternative and mild conditions in solution and on solid supports is of particular interest in natural product synthesis.