Study On The Application Of N, N'-disuccinimidyl Carbonate (DSC) In Peptide Synthesis

The peptides play important roles in life science. Dipeptides and their derivatives are also very important in life activity and applied in chembiology as enzymatic inhibitor especially for tumour. In this dissertation, synthetic method for diptide and new amido protective group are designed and studied.N,N'-disuccinimidyl carbonate (DSC) is designed and synthesized as an activated coupling reagent which can be used to synthesize peptides and their ramifications. At the mean while, menthyloxycarbonyl (MOC) as an N-protective group in amino acids is also investigated.N,N'-disuccinimidyl carbonate (DSC) being a new coupling reagent can simplify the process in order to make the reaction more economical. In the reaction, the triethylamine can bring partial racemate(10.2%), the N-methylmorphorline can reduce efficiently the degree of racemate(1.6%). Morever, using organic weak bases such as pyridine and N-methylmorphorline, the O,O'-diisopropyl phosphoryl amido protection group can avoid the peptide racemate which can detected by ³¹P NMR, HPLC .The menthyloxycarbonyl succimide (MOC-OSu), a potential amido protection reagent produced from L-(-)-menthol which have three stereo centers, can be planted to be crystal easily. In this thesis we use MOC-OSu to synthesize a series of white solid MOC-amino acids and MOC- dipeptide methyl esters in simple conditions and high yield. The result shows that the racemate is very low which was proved by NMR, HPLC. At the mean while, the MOC is very steady in the weak acid and alkali, but can be deprotected easily in strong acid such as trifluoroacetic acid.