Encoded oligonucleotide tags

Oligonucleotide encoding was reported by-Nielsen and colleagues [19], who used the construct presented in Fig. 2. a-Amino functionality of the serine residue was used as an attachment point for the growing peptide chain, while the (3-hydroxyl of the side chain was used for the encoding oligonucleotide assembly. Therefore, the tag-to-peptide ratio used in this work was 1 1. Synthesis was carried out on controlled porous glass (CPG) beads. 

Oligonucleotide tagging was developed and used successfully for the synthesis of peptides many methodological issues, related mostly to the chemical compatibility of the approach, were solved. However, the compatibility of this encoding strategy with the synthesis of other classes of organic molecules remains limited. 

Molecular tags overcome the chemical sensitivity and orthogonal protection required by both peptide and oligonucleotide encoding. Two such methods have been developed and applied to the synthesis of both peptide and nonoligomeric libraries. One of these [34] approaches uses chemically robust haloaromatic tags which are used in a binary encoding... 

The first encoding approaches used peptides (177) or oligonucleotides (178) as tags. We will consider two reported examples of resin-bound constructs able to support peptide-encoded (7.37, Fig. 7.25) (177) and oligonucleotide-encoded (7.38, Fig. 7.25) (179) peptide or peptidomimetic library synthesis. They both contain a core moiety, derived from L-lysine (7.37) or L-serine (7.38), which simultaneously multiphes the... 

Figure 1.10. Encoded combinatorial libraries by (A) sequenceable chemical tags (oligonucleotides and peptides) or by (B) non-sequenceable chemical tags (haloaromatic phenol ethers).

Using this method, several fluorescein- and biotin-tagged oligonucleotidic hybridization probes (a probe for the detection of genes encoding cysteine proteases of Fasciola hepatica, a probe for the detection of human papillomavirus (type 16)) have been synthesized and successfully used in biological studies. 

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