Synthesis of photolabile 5 '-O-phosphoramidites for the photolithographic production of microarrays of inversely oriented oligonucleotides

Citation
M. Beier et al., Synthesis of photolabile 5 '-O-phosphoramidites for the photolithographic production of microarrays of inversely oriented oligonucleotides, HELV CHIM A, 84(7), 2001, pp. 2089-2095
Citations number
17
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
84
Issue
7
Year of publication
2001
Pages
2089 - 2095
Database
ISI
SICI code
0018-019X(2001)84:7<2089:SOP5'F>2.0.ZU;2-2
Abstract
The photolabile 3 ' -O-{[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' - phosphoramidites (16-18) were synthesized (see Scheme) for an alternative m ode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in si tu DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the o rientation of enzymatic synthesis. Synthesis yields were as good as those o f conventional reactions. The resulting oligonucleotides are attached to th e: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are availa ble as substrates for enzymatic reactions such as primer extension upon hyb ridization of a DNA template (see Fig. 2). The production of such oligonucl eotide chips adds new procedural avenues to the growing number of applicati ons of DNA microarrays.