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US 6,747,142 B1Granted
Multiple methoxyoxalamido and succinimido precursors for nucleophilic addition
AssigneeFidelity Systems, Inc.
InventorNikolai N. Polouchine
Life of this patent
Estimating the term…
Abstract
Compounds and the synthesis of compounds containing multiple precursor groups and allowing the efficient synthesis of highly functionalized oligonucleotides and oligomers are provided. Also, a branching unit that helps to further increase the density of functional groups on synthetic oligonucleotides and oligomers is provided.
Claims37
A monomeric compound of formula (I) or of a salt of a compound of said formula (I):
- A—Xn (I)
- wherein A represents an organic moiety selected from the group consisting of a substituted or unsubstituted alkane having from 3 to 100 carbon atoms, a substituted or unsubstituted cycloalkane having from 3 to 12 carbon atoms, and a substituted or unsubstituted heterocyclic compound having from 3 to 20 carbon atoms;
- n is at least 2;
- and each X is independently selected from the group consisting of:
- —NRCOCONu, —NHCOCR2CR2CONu, —NHCOCR═CRCONu, —NHCOSSCONu, —NRCOCOOCR3,
- wherein Nu represents a nucleophile, each R independently represents H or a substituted or unsubstituted alkyl group, and where X is
- then at least one R is a substituted or unsubstituted alkyl group.
4 more elements
A method for forming a compound of formula (I) or a salt of said compound of formula (I):
- A—Xn (I)
- wherein A represents an organic moiety, n is at least 2, and each X is independently selected from the group consisting of:
- —NRCOCONu, —NHCOCR2CR2CONu, —NHCOCR═CRCONu, —NHCOSSCONu, —NRCOCOOCR3,
- wherein each R independently represents H or a substituted or unsubstituted alkyl group, and Nu represents a nucleophile, said method comprising:
- reacting, by nucleophilic addition, a first compound containing a first moiety selected from the group consisting of:
- —NRCOCOOCR3,
- wherein each R independently represents H or a substituted or unsubstituted alkyl group, with a second compound (HNu) containing at least three primary or secondary amino groups to form a third compound containing a second moiety selected from the group consisting of:
- —NRCOCONu, —NHCOCR2CR2CONu, —NHCOCR═CRCONu, and —NHCOSSCONu, wherein each R independently represents H or a substituted or unsubstituted alkyl group, wherein one of said at least three primary or secondary amino groups of said second compound acts as a nucleophile in said nucleophilic addition, leaving at least two unreacted primary or secondary amino groups in said second moiety;
- and
- reacting said third compound with at least two compounds, which may be the same or different, each containing a third moiety independently selected from the group consisting of:
- —COCOOCR3, —COCR2CR2CO—, —COCR═CRCO— and —COSSCO—, wherein each of said at least two compounds reacts with one of said at least two unreacted primary or secondary amino groups to form a compound containing at least two moieties independently selected from the group consisting of:
- —NRCOCOOCR3,
- wherein each R independently represents H or a substituted or unsubstituted alkyl group.
10 more elements
A monomeric compound of formula (II) or of a salt of a compound of said formula (II):
- wherein each Y independently represents H, a group that protects a hydroxy group, a phosphorus containing group, a group reactive to link hydroxy groups, or a phosphodiester linkage to another compound, B is a nitrogenous base, and R′ is an organic group that contains at least two functional groups independently selected from the group consisting of:
- —NRCOCONu, —NHCOCR2CR2CONu, —NHCOCR═CRCONu, —NHCOSSCONu, —NRCOCOOCR3,
- wherein each R independently represents H or a substituted or unsubstituted alkyl group, and Nu represents a nucleophile.
Dependencies are inferred from the claim text.