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Photocaging Strategy for Functionalisation of Oligonucleotides and Its Applications for Oligonucleotide Labelling and Cyclisation
Author(s) -
Su Meng,
Wang Jie,
Tang XinJing
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103833
Subject(s) - oligonucleotide , labelling , amine gas treating , solid phase synthesis , combinatorial chemistry , chemistry , thiol , protecting group , organic chemistry , dna , biochemistry , peptide , alkyl
We have used a photocaging strategy to develop novel phosphoramidites and expand the repertoire of protecting groups for modification of oligonucleotides by solid‐phase synthesis. We synthesised five photolabile phosphoramidites and four new photolabile controlled pore glasses (CPGs). By using these photolabile phosphoramidites and CPGs, modified oligodeoxynucleotides (ODNs) with phosphate, amine, acid, thiol and carbonyl moieties at 5′ and/or 3′ ends were readily synthesised. To the best of our knowledge, this is the first report of introducing a carbonyl at the 5′ end and thiol groups at both ends of ODNs with photolabile modifiers. Terminal labelling was also easily realised in solution or by on‐column solid‐phase synthesis. By using the photolabile amine modifier and the photolabile acid CPG, cyclisation of an oligodeoxynucleotide was achieved with good yields. This study provides an alternative way to introduce functional groups into oligonucleotides and expand the scope of oligonucleotide bio‐orthogonal labelling.