151322-48-4Relevant academic research and scientific papers
Incorporation of 8-histaminyldeoxyadenosine 18-(2-(4-imidazolyl)ethylamino)-2'-deoxyriboadenosine] into oligodeoxyribonucleotides by solid phase phosphoramidite coupling.
Lermer, Leonard,Hobbs, John,Perrin, David M
, p. 651 - 664 (2002)
The 3'phosphoramidite of 8-histaminyl deoxyadenosine has been prepared and successfully incorporated into a short oligodeoxyribonucleotide. The synthetic methodology leading to this preparation is given and the implications for developing new DNAzymes as
Site-specific functionalization with amino, guanidinium, and imidazolyl groups enabling the activation of 10-23 DNAzyme
Chai, Zhilong,Du, Shanshan,He, Junlin,Li, Yang,Shi, Weiguo
supporting information, p. 19067 - 19075 (2020/06/08)
10-23 DNAzyme has been extensively explored as a therapeutic and biotechnological tool, as well as in DNA computing. Faster cleavage or transformation is always needed. The present research displays a rational modification approach for a more efficient DNAzyme. In the catalytic core, amino, guanidinium and imidazolyl groups were introduced for its chemical activation through the adenine base. Among the six adenine residues, A9 is the unique residue that realizes all the positive effects; the 6-amino and 8-position of adenine and the 7-position of 8-aza-7-deaza-adenine could be used for the introduction of the functional groups. A12 is a new choice for catalytic improvement with an 8-substituent. Therefore, more active DNAzymes could be expected by this nucleobase-modified activation approach.
Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine
Prakash,Krishna Kumar,Ganesh
, p. 4035 - 4050 (2007/10/02)
Dinucleotides (Figure 1b-d) possessing histamino/ethylenediamino substituents at C8 of adenine have been synthesised for modelling the molecular interactions that occur at catalytic site of nucleases. These compounds have been designed for putative molecular recognition of internucleotide phosphate by a complementary group (imidazole/-NH2) in the pendant C-8 side chains. 1H NMR spectroscopic analysis of synthesised model compounds indicate that C-8 modification leads to increase in percentage of S conformation of modified sugar while still maintaining an anti glycosyl torsion as in unmodified analog d(TpA). The C-8 side chain functionality (histamine/ethylenediamine) is probably involved in intramolecular interaction (electrostatic/ hydrogen bond) with the phosphate and/or 2′OH in (14). Such predisposition of side chain catalytic groups is important in developing appropriate models for active site of nucleases.
