Synthesis and Structure Analysis of a Tripeptide Containing N-methyl Group Amino Acid  

作　　者：甄小丽 马振杰 田霞 李营 韩建荣 刘守信 

机构地区：[1]College of Sciences, Hebei University of Science & Technology [2]College of Chemical & Pharmaceutical Engineering, Hebei University of Science &Technology

出　　处：《Chinese Journal of Structural Chemistry》2016年第5期718-724,共7页结构化学（英文）

基　　金：supported by the National Natural Science Foundation of China(No.21272052,21472034);Natural Science Foundation of Hebei Province(No.14272604D B2014208138);the Foundation of the Education Department of Hebei Province(No.ZH2012025,ZD2014017);National Basic Research Program of China(2011CB512007 and 2012CB723501)

摘　　要：A convenient method of synthesizing a tripeptide-containing N-methyl group amino acid was developed using O-benzotriazole-N,N,N＇,N＇-tetramethyluronium-hexafluorophosphate as the condensing agent. The crystals of tripeptide had white needles belonging to the orthorhombic space group P2_12_12_1. The conformational preference for homochiral tripeptides with one N-methylated amide bond was also investigated. Crystal-structure analysis showed that homochiral tripeptides with an internal N-methylated amide bond preferred a trans-amide form, thereby giving the peptide β-fold characteristics. Intermolecular C-H···O and N-H···O hydrogen bonds linked the molecules into a one-dimensional chain and stabilized the structure.A convenient method of synthesizing a tripeptide-containing N-methyl group amino acid was developed using O-benzotriazole-N,N,N＇,N＇-tetramethyluronium-hexafluorophosphate as the condensing agent. The crystals of tripeptide had white needles belonging to the orthorhombic space group P2_12_12_1. The conformational preference for homochiral tripeptides with one N-methylated amide bond was also investigated. Crystal-structure analysis showed that homochiral tripeptides with an internal N-methylated amide bond preferred a trans-amide form, thereby giving the peptide β-fold characteristics. Intermolecular C-H···O and N-H···O hydrogen bonds linked the molecules into a one-dimensional chain and stabilized the structure.

关 键 词：tripeptide N-methyl amino acid synthesis crystal structure hydrogen bond 

分 类 号：O629.72[理学—有机化学]