Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA.
The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycoprotein pull-down, inhibition of hydrolytic enzymes and boron neutron capture therapy. The incorporation of the boronic-acid group into DNA could lead to molecules of various biological functions. We have successfully synthesized a boronic acid-labeled thymidine triphosphate (B-TTP) linked through a 14-atom tether and effectively incorporated it into DNA by enzymatic polymerization. The synthesis was achieved using the Huisgen cycloaddition as the key reaction. We have demonstrated that DNA polymerase can effectively recognize the boronic acid-labeled DNA as the template for DNA polymerization, that allows PCR amplification of boronic acid-labeled DNA. DNA polymerase recognitions of the B-TTP as a substrate and the boronic acid-labeled DNA as a template are critical issues for the development of DNA-based lectin mimics via in vitro selection.
Lin
Na
N
Department of Chemistry and Center for Biotechnology and Drug Design, Campus Box 4098, Georgia State University, Atlanta, GA 30302-4098, USA.
Yan
Jun
J
Huang
Zhen
Z
Altier
Craig
C
Li
Minyong
M
Carrasco
Nicolas
N
Suyemoto
Mitsu
M
Johnston
Lynette
L
Wang
Siming
S
Wang
Qian
Q
Fang
Hao
H
Caton-Williams
Julianne
J
Wang
Binghe
B
D052157:Aptamers, Nucleotide / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D004247:DNA / Q000096:biosynthesis* / Q000737:chemistry; D017931:DNA Primers; D004259:DNA-Directed DNA Polymerase / Q000378:metabolism; D016133:Polymerase Chain Reaction; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013698:Templates, Genetic; D013942:Thymine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D052157:Aptamers, Nucleotide; D001896:Boron Compounds; D017931:DNA Primers; D013942:Thymine Nucleotides; D004247:DNA; D004259:DNA-Directed DNA Polymerase