Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Charge-Transfer Effect in Solid Phase Peptide Synthesis: Unsusally High Reactivity in Peptide Bond Formation between p-Nitrobenzophenone Oxime Resin Ester and Amino Acid 4-(Methylthio)phenyl Ester

  • Park, Dong-Hyun (Department of Chemical Technology, College of Engineering, Seoul National University) ;
  • Jung, Jae-Kyu (Department of Chemical Technology, College of Engineering, Seoul National University) ;
  • Lee, Yoon-Sik (Department of Chemical Technology, College of Engineering, Seoul National University)
  • Published : 1988.12.20
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Abstract

Unusually high reactivity was found in peptide bond formation between p-nitrobenzophenone oxime resin (I) ester and amino acid 4-(methylthio)phentyl (MTP) esters. A charge-transfer complex between the two phenyl rings of the oxime resin (I) and the incoming amino acid MTP esters was considered to be responsible to accelerate the aminolysis reaction of the peptide oxime resin ester. Several di-, tri-, and pentapeptide fragments for preparing enkephalin and glutathione oligomers were successfully prepared in short times.

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References

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