Synthesis And Properties Of Pentapeptide And Tripeptide

Invasion and metastasis are the essential characteristics of cancer and the main factors of tumor patients mortality.At present,the inhibition of tumor cell adhesion is a good method to suppress the invasion and metastasis of tumor cells.Some synthetic peptides have the specific anti-adhesion and then are used to inhibit the invasion and metastasis of tumor cells.These peptides include the conservative sequence of Arg-Gly-Asp tripeptide from matrix proteins,Tyr-Ile-Gly-Ser-Arg pentapeptide from laminin of the basement membrane and Glu-Ile-Leu-Asp-Val pentapeptide from fibaonectin.The main contents of this thesis were summarized as follows:1.The development and application of amino acids and peptides were reviewed briefly.The categorization and selection of protected groups to amino acids,the main function and the synthetic methods of peptides were described in detail.2.N-butoxycarboxylation-L-glycine was prepared by the protection reaction of L-glycine with N-tert-butoxycarboxylation.L-aspartate acid 1,4-dibenzyl easter p-toluenesulfonate was made from L-aspartate protected by benzyl groups.Then the fully protected dipeptide(GD)was synthesized by the resction between N-butoxycarboxylation-L-glycine and L-aspartate acid 1,4-dibenzyl ester p-toluenesulfonate.Subsequently,Arg-Gly-Asp tripeptide(RGD)was synthesized by the reation between GD dipeptide and N-butoxycarboxylation-N-nitro-L-arginine.These compounds obtained were further characerized by 1HNMR,FT-IR,UV and MS.Experimented data proved the formation of RGD tripeptide.3.The fully protected dipeptide(SR)was synthesized by the reaction between N-butoxycarboxylation-O-benzyl-L-serine and N-nitro-L-arginine benzyl ester Meanwhile,the fully protected tripeptide(YIG)was also synthesized by the reaction of N-butoxycarboxylation-L-isoleucine,benzyl-glycine-4-methylbenesulfonate and N-butoxycarboxylation-L-tyrosine.Subsequently,Tyr-Ile-Gly-Ser-Arg pentapeptide(YIGSR)was synthesized by the reaction between the fully protected dipaptide(SR)and tripeptide(YIG).These compounds obtained were further characerized by 1HNMR,FT-IR,UV and MS.Experimented results indicated the formation of YIGSR pentapeptide.