Abstract:
:We report the synthesis of new phosphoramidite building blocks and their use for the modification of oligonucleotides with hydrazides. The reaction of these hydrazide oligonucleotides with active esters and aldehydes is demonstrated for solution conjugation and immobilization. Compared with the established amino modified oligonucleotides, hydrazides show enhanced reactivity at neutral and acidic buffer conditions. One method to introduce hydrazides is using amidites with preformed, protected hydrazides. A completely novel approach is the generation of the hydrazide functionality during the oligonucleotide cleavage and deprotection with hydrazine. Therefore, building blocks for the introduction of esters as hydrazide precursors are described. For the enhanced attachment on surfaces branched modifier amidites, which introduce up to four reactive groups to the oligonucleotide, are applied. The efficiency of branched hydrazide oligonucleotides compared with standard amino modified oligonucleotides for the immobilization of DNA on active electronic Nanogen chips is demonstrated.
journal_name
Nucleic Acids Resjournal_title
Nucleic acids researchauthors
Raddatz S,Mueller-Ibeler J,Kluge J,Wäss L,Burdinski G,Havens JR,Onofrey TJ,Wang D,Schweitzer Mdoi
10.1093/nar/gkf594keywords:
subject
Has Abstractpub_date
2002-11-01 00:00:00pages
4793-802issue
21eissn
0305-1048issn
1362-4962journal_volume
30pub_type
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