Modified phosphorous intermediates for providing functional...

C - Chemistry – Metallurgy – 07 – H

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C07H 21/04 (2006.01) C07C 69/78 (2006.01) C07C 323/12 (2006.01) C07C 323/16 (2006.01) C07D 317/20 (2006.01) C07F 9/24 (2006.01) C07F 9/655 (2006.01) C07H 21/00 (2006.01) C07K 14/00 (2006.01) C08G 69/10 (2006.01)

Patent

CA 2073846

Phosphoramidites of the formula Image where R is a base-labile: protecting group, R1 and R2 are individually alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, or aryl of 6 to 20 carbon atoms or are joined together to form with the nitrogen atom a cyclic structure of 4-7 carbon atoms and 0 to 1 annular chalcogen atoms of atomic number 8 to 16, G is a hydrocarbylene group of 1 to 20 carbon atoms and Z is a hydroxy-protected vicinal diol group bound to G by one of the vicinal diol carbon atoms or a disulfide group and bound to G by one of the sulfur atoms of the disulfide group, with the proviso that G is of at least 4 carbon atoms when Z is said disulfide group are used in conventional automated oligonucleotide synthesis to introduce a functional aldehyde or thiol group on the 5' end of the oligonucleotide to thereby provide a reactive site on the oligonucleotide that may be used to conjugate the oligonucleotide to molecules that contain a free amino group or an electrophilic center reactive with a thiol group.

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