Dl. Mcminn et Mm. Greenberg, NOVEL SOLID-PHASE SYNTHESIS SUPPORTS FOR THE PREPARATION OF OLIGONUCLEOTIDES CONTAINING S3'-ALKYL AMINES, Tetrahedron, 52(11), 1996, pp. 3827-3840
?he synthesis and application of photolabile supports for solid phase
oligonucleotide synthesis that release oligonucleotides containing 3'-
alkyl amines is described. The alkyl amine functionality can be reveal
ed without removing any other protecting groups throughout the biopoly
mer. The solid phase synthesis supports do not contain a nucleoside, m
aking it possible to use a single support for the synthesis of oligonu
cleotides independent of their sequence. Individual solid phase synthe
sis supports differ according to the length of the alkyl tether betwee
n the 4,4'-dimethoxytrityl group which serves as the initiation site f
or oligonucleotide synthesis and the latent alkyl amine. Eicosameric o
ligonucleotides are obtained in yields ranging from 70-98% under photo
lysis conditions that are known to produce less than 3% thymidine thym
idine photodimers. Longer oligonucleotides (30 and 40 nucleotides in l
ength) are cleaved from these solid phase synthesis supports in lower
yields.