26889-39-4

Usage

Uses

Used in Nucleic Acid Synthesis:
2'-Amino-D-uridine is used as a building block for the synthesis of nucleic acids, such as RNA and DNA, due to its ability to improve the stability and binding affinity of these molecules.
Used in Pharmaceutical Industry:
2'-Amino-D-uridine is used as a key component in the development of nucleic acid-based therapeutics. Its enhanced stability and binding affinity make it a promising candidate for the design of drugs targeting specific genetic sequences or RNA structures.
Used in Diagnostics:
2'-Amino-D-uridine is used as a component in the development of diagnostic tools, such as probes and sensors, that rely on the specific recognition and binding of nucleic acid sequences.
Used in Research and Development:
2'-Amino-D-uridine is used as a research tool for studying the structure and function of RNA molecules. Its ability to form additional hydrogen bonds and interactions with other nucleotides allows researchers to investigate the role of specific modifications in RNA stability, folding, and function.

Upstream product

• 847911-24-4 guanosyl-(3',3')-(2'-amino-2'-deoxyuridine) 
• 26929-65-7 2'-azido-2'-deoxyuridine 

Downstream Products

• 60966-26-9 2'-amino-2'-deoxyguanosine 
• 76727-51-0 9-(2-amino-2-deoxy-β-D-ribofuranosyl)-2-chlorohypoxanthine 
• 171502-14-0 2'-deoxy-2'-(3-methoxybenzamido)uridine 
• 182626-48-8 1-[2-(benzyloxycarbonyl)amino-2-deoxy-β-D-ribofuranosyl]uracil 
• 1261083-58-2 2'-deoxy-2'-[3-(2-furyl)-2-azapropanamido]-5'-O-(4,4-dimethoxytrityl)uridin-3'-yl-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 1312415-82-9 C₃₆H₃₆N₄O₉ 
• 282543-37-7 2,2-dimethyl-propionic acid 3-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylcarbamoyl]-2-oxo-2H-chromen-7-yl ester 
• 282543-36-6 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid [5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl]-amide 
• 333998-14-4 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid [(2R,3R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl]-amide 
• 501353-62-4 2'-N-(N-allyloxycarbonylphenylalanyl)-2'-amino-2'-deoxy-5'-dimethoxytrityluridine 
• 807370-40-7 2'-[N,N-bis(2-methoxyoxalylaminoethyl)aminoethyl]-5'-O-(4,4'-dimethoxytrityl)aminooxalylamino-2'-deoxyuridine 
• 177980-14-2 5'-O-(4,4'-dimethoxytrityl)-2'-methoxyoxalylamido-3'-(2-cyanoethyl-N,N-diisopropylamino)phosphinyl-2'-deoxyuridine 
• 177980-12-0 5'-O-(4,4'-dimethoxytrityl)-2'-methoxyoxalylamido-2'-deoxyuridine 
• 118849-17-5 5'-O-(4,4'-dimethoxytrityl)-2'-(trifluoroacetylamido)-2'-deoxyuridine 

Relevant academic research and scientific papers

Phosphodiester cleavage of guanylyl-(3′,3′)-(2′-amino- 2′-deoxyuridine): Rate acceleration by the 2′-amino function

Hydrolytic reactions of the structural analogue of guanylyl-(3′, 3′)-uridine, guanylyl-(3′,3′)-(2′-amino-2′- deoxyuridine), having one of the 2′-hydroxyl groups replaced with an amino function, have been followed by RP HPLC in the pH range 0-13 at 90°C. The results are compared to those obtained earlier with guanylyl-(3′,3′) -uridine, guanylyl-(3′,3′)-(2′,5′-di-O-methyluridine), and uridylyl-(3′,5′)-uridine. Under basic conditions (pH > 8), the hydroxide ion-catalyzed cleavage of the P-O3′ bond (first-order in [OH-]) yields a mixture of 2′-amino-2′-deoxyuridine and guanosine 2′,3′-cyclic phosphate which is hydrolyzed to guanosine 2′- and 3′-phosphates. Under these conditions, guanylyl-(3′, 3′)-(2′-amino-2′-deoxyuridine) is 10 times less reactive than guanylyl-(3′,3′)-uridine. Under acidic and neutral conditions (pH 3-8), where the pH-rate profile for the cleavage consists of two pH-independent regions (from pH 3 to pH 4 and from 6 to 8), guanylyl-(3′,3′)- (2′-amino-2′-deoxyuridine) is considerably reactive. For example, in the latter pH range, guanylyl-(3′,3′)-(2′-amino-2′- deoxyuridine) is more than 2 orders of magnitude more labile than guanylyl(3′,3′)-(2′,5′-di-O-methyluridine), while in the former pH range the reactivity difference is 1 order of magnitude. Under very acidic conditions (pH +]) compete with the cleavage. The Zn2+-promoted cleavage ([Zn2+] = 5 mmol L-1) is 15 times faster than the uncatalyzed reaction at pH 5.6. The mechanisms of the reactions of guanylyl-(3′,3′)-(2′-amino-2′-deoxyuridine) are discussed, particularly focusing on the possible stabilization of phosphorane intermediate and/or transition state via an intramolecular hydrogen bonding by the 2′-amino group.

Efficient reduction of azides to amines with tributylstannane. High-yield syntheses of amino and diamino deoxynucleosides

Treatment of unprotected azido-deoxynucleosides with tributylstannane/AIBN in hot benzene/DMAC (or silyl-protected derivatives in benzene) resulted in formation of the corresponding amino-deoxynucleosides in high isolated yields. A radical process is indicated.