N-cyclohexyl-N'-isopropylcarbodiimide: a hybrid that combines the structural features of DCC and DIC.
N-Cyclohexyl-N'-isopropylcarbodiimide was prepared and used for peptide couplings by various procedures. Reaction between Z-Val and Gly-OEt was used for yield studies and determination of the extent of the side reaction in solution. The value of this reagent for solid peptide synthesis was demonstrated by the synthesis of sequences comprising the 65-74 residues of acyl carrier protein. The efficiency of activation was determined by competition experiments. From all these studies the conclusion can be drawn that N-cyclohexyl-N'-isopropylcarbodiimide is comparable to or even better than the commonly used DCC for mediation of peptide bond formation in solid phase synthesis. By virtue of the solubility of N-cyclohexyl-N'-isopropylurea in dichloromethane, the carbodiimide seems to be a good candidate for practical execution of peptide bond formation by the standard carbodiimide procedure.
Izdebski
J
J
Department of Chemistry, University of Warsaw, Poland.
Pachulska
M
M
Orłowska
A
A
D002234:Carbodiimides / Q000138:chemical synthesis* / Q000737:chemistry*; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*; D012995:Solubility; D013329:Structure-Activity Relationship
D002234:Carbodiimides; D010455:Peptides; C092679:N-cyclohexyl-N'-isopropylcarbodiimide; D004024:Dicyclohexylcarbodiimide; C081611:1,3-diisopropylcarbodiimide