Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA

Click Reactions and Boronic Acids: Applications, Issues, and Potential Solutions

“…Therefore, boronic acid-modified TTP analogs were prepared for DNA aptamer selection and other applications. Specifically, an 8-quinolynylboronic acid-modified thymidine-5'-triphosphate ( QB-TTP , Scheme 1 ) was first synthesized by the Wang lab [ 52 ]. In accomplishing the synthesis, there were two dilemmas.…”

“…Among all the biologically active boronic acids, bortezomib is an FDA-approved anticancer agent [ 43 ]. In chemical biology, boronic acids are used in the detection and sensing of peroxides [ 44 , 45 ], recognition and sensing of the tetraserine motif in protein [ 46 ], development of new MRI contrast agents [ 47 , 48 ], cell-surface carbohydrate biomarker recognition [ 49 , 50 , 51 ], and development of boronic acids-modified aptamers [ 52 , 53 ] and boronic acid-modified proteins for various sensing and purification applications [ 54 ].…”

Carbohydrate biomarkers for future disease detection and treatment

“…The Wang lab is working on incorporating boronic acid-modified thymidine into DNA for aptamer selection work for glycoproteins. A boronic acid-labeled thymidine triphosphate (BTTP 9, Figure 6) was successfully synthesized [46]. It has been demonstrated that DNA polymerase can recognize BTTP as a substrate and the boronic acid-labeled DNA as a template, which are critical issues for aptamer selection work.…”

“…As a result, recent advancements in glycobiology and glycomics have also opened new doors for the development of new therapeutics and imaging agents through carbohydrate recognition. Therefore, compounds that can specifically recognize a particular carbohydrate have very important applications [41][42][43][44][45][46][47][48][49][50][51][52]. They can be used as sensors for detection, diagnosis, and prognosis, as "blockers/inhibitors" for therapeutics development if the target carbohydrate is involved in pathogenesis, and as vectors for the targeted delivery of imaging and therapeutic agents.…”

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization

“…In addition to their role in these fundamental biological transformations, their modified counterparts have advanced as a versatile and mild platform for the introduction of functional groups into oligonucleotides, a methodology that nicely complements the automated solid-phase synthesis that is usually applied 1,2 . Indeed, provided the (d)NTPs can act as substrates for RNA and DNA polymerases 3 , a wealth of functional groups including amino acids [4][5][6][7][8][9][10][11][12][13] , boronic acids 14,15 , nornbornene 16 , diamondoid-like residues 17 , side-chains for organocatalysis 18 , bile acids 19 , and even oligonucleotides 20 can be introduced into oligonucleotides.…”