Nucleic Acids Research, Vol 26, Issue 19 4309-4314, Copyright © 1998 by Oxford University Press
C Bailly and MJ Waring
2,6-Diaminopurine (DAP) is an analogue of adenine which can be converted to
nucleotides that serve as substrates for incorporation into nucleic acids
by polymerases in place of (d)AMP. It pairs with thymidine (or uracil),
engaging in three hydrogen bonds of the Watson- Crick type. The result of
DAP incorporation is to add considerable stability to the double helix and
to impart other structural features, such as an altered groove width and
disruption of the normal spine of hydration. DNA containing DAP may or may
not be recognized by restriction endonucleases; RNA containing DAP may not
engage in normal splicing. The DAP.T pair affects the local flexibility of
DNA and impedes the interaction with helix bending proteins. By providing a
non- canonical hydrogen bond donor in the minor groove and/or blocking
access to the floor of that groove it strongly affects interactions with
small molecules such as antibiotics and anticancer drugs. Examples which
illustrate altered recognition of nucleotide sequences in DAP- containing
DNA are presented: changed sites of cutting by bleomycin, photocleavage by
uranyl nitrate and footprinting with mithramycin. Using DNA in which both
A-->DAP and G-->Inosine substitutions have been made it is possible
to assess precisely the role of the purine 2-amino group in ligand-DNA
recognition.
REVIEWS
The use of diaminopurine to investigate structural properties of nucleic acids and molecular recognition between ligands and DNA
INSERM U-124 et Laboratoire de Pharmacologie Antitumorale du Centre Oscar Lambret, IRCL, Place de Verdun, 59045 Lille, France. bailly@lille.inserm.f
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