New solid support for the synthesis of 3'-oligonucleotide conjugates through glyoxylic oxime bond formation.
A novel solid support 1 was synthesized to incorporate glyoxylic aldehyde functionality at the oligonucleotide 3'-terminus. 6-mer and 11-mer oligonucleotide sequences containing 3'-glyoxylic aldehyde functionality were prepared by using this support. These modified oligonucleotides were coupled to reporters containing an aminooxy group to prepare oligonucleotide 3'-conjugates through glyoxylic oxime bond formation. The hydrolytic stability of a glyoxylic oxime linkage was also investigated. [reaction: see text].
Spinelli
Nicolas
N
Département de Chimie Moléculaire, UMR CNRS 5250, ICMG FR2607, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.
Edupuganti
Om Prakash
OP
Defrancq
Eric
E
Dumy
Pascal
P
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006038:Glyoxylates / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D006038:Glyoxylates; D009841:Oligonucleotides; D010091:Oximes; D010455:Peptides