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PDBsum entry 4rt2
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Transferase/DNA
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PDB id
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4rt2
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References listed in PDB file
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Key reference
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Title
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Two scaffolds from two flips: (α,β)/(β,γ) Ch2/nh "met-Im" analogues of dttp.
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Authors
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A.P.Kadina,
B.A.Kashemirov,
K.Oertell,
V.K.Batra,
S.H.Wilson,
M.F.Goodman,
C.E.Mckenna.
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Ref.
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Org Lett, 2015,
17,
2586-2589.
[DOI no: ]
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PubMed id
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Abstract
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Novel α,β-CH2 and β,γ-NH (1a) or α,β-NH and β,γ-CH2 (1b)
"Met-Im" dTTPs were synthesized via monodemethylation of
triethyl-dimethyl phosphorimido-bisphosphonate synthons (4a, 4b), formed via a
base-induced [1,3]-rearrangement of precursors (3a, 3b) in a reaction with
dimethyl or diethyl phosphochloridate. Anomerization during final
bromotrimethylsilane (BTMS) deprotection after Mitsunobu conjugation with dT was
avoided by microwave conditions. 1a was 9-fold more potent in inhibiting DNA
polymerase β, attributed to an NH-group interaction with R183 in the active
site.
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