NOVEL REAGENTS FOR UNIVERSAL SITE-SPECIFIC LABELING AND MODIFICATIONS OF NUCLEIC ACIDS
First Claim
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1. A method for modifying an oligonucleotide, comprising:
- (a) conjugating H2N(CH2)nNH2 to the 5′
end of the oligonucleotide to form a conjugated product;
(b) amidating a free —
NH2 group of the conjugated product with R1—
N3; and
(c) reacting the terminal —
N3 group with one of HC≡
C—
R2 and a cycloalkyne, wherein n is an integer from 2 to 6, R1 is a first substituent, and R2 is a second substituent.
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Abstract
The present invention discloses a method of harnessing versatile phosphoramidation reactions to regioselectively incorporate alkynyl/azido groups into post-synthetic nucleic acids primed with phosphate at the 5′ termini. With and without the presence of copper, the modified nucleic acids were subjected to azide-alkyne cycloaddition to obtain various nucleic acid conjugates including a peptide-oligonucleotide conjugate (POC) with a high yield.
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Citations
17 Claims
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1. A method for modifying an oligonucleotide, comprising:
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(a) conjugating H2N(CH2)nNH2 to the 5′
end of the oligonucleotide to form a conjugated product;(b) amidating a free —
NH2 group of the conjugated product with R1—
N3; and(c) reacting the terminal —
N3 group with one of HC≡
C—
R2 and a cycloalkyne, wherein n is an integer from 2 to 6, R1 is a first substituent, and R2 is a second substituent. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
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9. A method for modifying an oligonucleotide, comprising:
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(a) conjugating H2N(CH2)nNH2 to the 5′
end of the oligonucleotide to form a conjugated product;(b) amidating a free —
NH2 group of the conjugated product with R1—
C≡
CH; and(c) reacting the alkyne group with R4—
N3, wherein n is an integer from 2 to 6, R1 is a first substituent, and R4 is a second substituent. - View Dependent Claims (10, 11, 12, 13)
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14. A method for modifying a nucleic acid, comprising:
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(a) conjugating H2N(CH2)nNH2 to the 5′
end of the nucleic acid to form a conjugated product;(b) reacting a free -NH2 group of the conjugated product with R—
N3 and R′
—
C≡
CH to form a nucleic acid compound. - View Dependent Claims (15, 16, 17)
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Specification