31010-60-3Relevant articles and documents
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Forrest,Walker
, p. 79,83 (1949)
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Sulfur incorporation generally improves Ricin inhibition in pterin-appended glycine-phenylalanine dipeptide mimics
Wiget, Paul A.,Manzano, Lawrence A.,Pruet, Jeff M.,Gao, Grace,Saito, Ryota,Monzingo, Arthur F.,Jasheway, Karl R.,Robertus, Jon D.,Anslyn, Eric V.
supporting information, p. 6799 - 6804 (2014/01/06)
Several 7-aminoamido-pterins were synthesized to evaluate the electronic and biochemical subtleties observed in the 'linker space' when N-{N-(pterin-7-yl)carbonylglycyl}-l-phenylalanine 1 was bound to the active site of RTA. The gylcine-phenylalanine dipeptide analogs included both amides and thioamides. Decarboxy gly-phe analog 2 showed a 6.4-fold decrease in potency (IC50 = 128 μM), yet the analogous thioamide 7 recovered the lost activity and performed similarly to the parent inhibitor (IC50 = 29 μM). Thiourea 12 exhibited an IC50 nearly six times lower than the oxo analog 13. All inhibitors showed the pterin head-group firmly bound in their X-ray structures yet the pendants were not fully resolved suggesting that all pendants are not firmly bound in the RTA linker space. Calculated log P values do not correlate to the increase in bioactivity suggesting other factors dominate.
Pteridines. I. β keto sulfoxides and α keto aldehyde hemithioacetals as pteridine precursors. A new selective synthesis of 6 and 7 substituted pteridines
Rosowsky,Chen
, p. 2073 - 2077 (2007/10/09)
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