title: Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA.
abstract: 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.
authors.affiliation: Department of Chemistry and Center for Biotechnology and Drug Design, Campus Box 4098, Georgia State University, Atlanta, GA 30302-4098, USA.
authors.forename: Na
authors.initials: N
authors.lastname: Lin
authors.forename: Jun
authors.initials: J
authors.lastname: Yan
authors.forename: Zhen
authors.initials: Z
authors.lastname: Huang
authors.forename: Craig
authors.initials: C
authors.lastname: Altier
authors.forename: Minyong
authors.initials: M
authors.lastname: Li
authors.forename: Nicolas
authors.initials: N
authors.lastname: Carrasco
authors.forename: Mitsu
authors.initials: M
authors.lastname: Suyemoto
authors.forename: Lynette
authors.initials: L
authors.lastname: Johnston
authors.forename: Siming
authors.initials: S
authors.lastname: Wang
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Hao
authors.initials: H
authors.lastname: Fang
authors.forename: Julianne
authors.initials: J
authors.lastname: Caton-Williams
authors.forename: Binghe
authors.initials: B
authors.lastname: Wang
mesh_terms: 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
chemical_list: D052157:Aptamers, Nucleotide; D001896:Boron Compounds; D017931:DNA Primers; D013942:Thymine Nucleotides; D004247:DNA; D004259:DNA-Directed DNA Polymerase