Phosphoramidite derivatives of macrocycles
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Abstract
The invention is directed to phosphoramidite derivatives of macrocycles, such as porphyrins and expanded porphyrins, including sapphyrins and texaphyrins. The phosphoramidite derivatives are useful as intermediates in the preparation of macrocycle-oligonucleotide conjugates.
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Citations
12 Claims
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1. A phosphoramidite derivative of an expanded porphyrin.
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2. A phosphoramidite derivative of a sapphyrin.
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3. A phosphoramidite derivative of a sapphyrin, said derivative having the following formula III:
- ##STR8## wherein, each of R1 -R10 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group, a ketone group, carboxyl, phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, sulfate-substituted alkyl, phosphoramidityl, alkylphosphoramidityl, alkoxyphosphoramidityl, the group --(CH2)t --O--W where W is hydrogen or a protecting group and t is an integer less than or equal to 10, or the group --(CH2)x --A--(CH2)y --B, where A is CH2, O, S, NH or NR11, where R11 is alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group a ketone group, carboxyl phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, or sulfate-substituted alkyl, COO, CONH, CSNH, or CONR11 ;
B is selected from the values of A, aryl, silyl, siloxy, aminoaryl, amino, amidoaryl, sugar, sugar derivative, polysaccharide, metal chelating group, alkylating agent, steroid, steroid derivative, amino acid, peptide, or polypeptide; and
each of x and y is independently an integer of less than or equal to 10 or are zero;
with the proviso that one of R1 -R10 is phosphoramidityl, alkylphosphoramidityl, or alkoxyphosphoramidityl. - View Dependent Claims (4, 5, 6, 7, 8)
- ##STR8## wherein, each of R1 -R10 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group, a ketone group, carboxyl, phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, sulfate-substituted alkyl, phosphoramidityl, alkylphosphoramidityl, alkoxyphosphoramidityl, the group --(CH2)t --O--W where W is hydrogen or a protecting group and t is an integer less than or equal to 10, or the group --(CH2)x --A--(CH2)y --B, where A is CH2, O, S, NH or NR11, where R11 is alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group a ketone group, carboxyl phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, or sulfate-substituted alkyl, COO, CONH, CSNH, or CONR11 ;
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9. A phosphoramidite derivative of a sapphyrin having the following formula:
- ##STR9## wherein, n is zero or an integer less than or equal to 10;
z is an integer less than or equal to 10; and each of R1 -R3 and R5 -R10 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group, a ketone group, carboxyl, phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, sulfate-substituted alkyl, the group --(CH2)t --O--W where W is hydrogen or a protecting group and t is an integer less than or equal to 10, or the group --(CH2)x --A--(CH2)y --B, where A is CH2, O, S, NH or NR11, where R11 is alkyl, alkenyl, alkynyl, halo, haloalkyl, hydroxyalkyl, glycol, polyglycol, thiol, alkyl thiol, aminoalkyl, carboxyalkyl, alkoxyalkyl, aryloxyalkyl, alkyloxycarbonyl, aryloxycarbonyl, CHO--, an ether group, a ketone group, carboxyl, phosphate, phosphonate, sulfate, phosphate-substituted alkyl, phosphonate-substituted alkyl, or sulfate-substituted alkyl, COO, CONH, CSNH, or CONR11 ;
B is selected from the values of A, aryl, silyl, siloxy, aminoaryl, amino, amidoaryl, sugar, sugar derivative, polysaccharide, metal chelating group, alkylating agent, steroid, steroid derivative, amino acid, peptide, or polypeptide; and
each of x and y is independently an integer of less than or equal to 10 or are zero. - View Dependent Claims (10, 11)
- ##STR9## wherein, n is zero or an integer less than or equal to 10;
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12. A phosphoramidite derivative of a porphyrin.
Specification