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PDBsum entry 4ce3
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References listed in PDB file
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Key reference
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Title
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Synthesis of macrolactam analogues of radicicol and their binding to heat shock protein hsp90.
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Authors
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B.L.Dutton,
R.R.Kitson,
S.Parry-Morris,
S.M.Roe,
C.Prodromou,
C.J.Moody.
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Ref.
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Org Biomol Chem, 2014,
12,
1328-1340.
[DOI no: ]
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PubMed id
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Abstract
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A series of macrolactam analogues of the naturally occurring resorcylic acid
lactone radicicol have been synthesised from methyl orsellinate in 7 steps,
involving chlorination, protection of the two phenolic groups, and hydrolysis to
the benzoic acid. Formation of the dianion and quenching with a Weinreb amide
results in acylation of the toluene methyl group that is followed by amide
formation and ring closing metathesis to form the macrocyclic lactam. Final
deprotection of the phenolic groups gives the desired macrolactams whose binding
to the N-terminal domain of yeast Hsp90 was studied by isothermal titration
calorimetry and protein X-ray crystallography.
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