Citation: ZHEN Xiao-Li, MA Zhen-Jie, TIAN Xi, LI Ying, HAN Jian-Rong, LIU Shou-Xin. Synthesis and Structure Analysis of a Tripeptide Containing N-methyl Group Amino Acid[J]. Chinese Journal of Structural Chemistry, ;2016, 35(5): 718-724. doi: 10.14102/j.cnki.0254-5861.2011-0919 shu

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

ZHEN Xiao-Li ^a ,
MA Zhen-Jie ^a ,
TIAN Xi ^a ,
LI Ying ^b ,
HAN Jian-Rong ^a,, ,
LIU Shou-Xin ^b,,

a.
a. College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, China;
b.
b. College of Chemical & Pharmaceutical Engineering, Hebei University of Science &Technology, Shijiazhuang 050018, China

Corresponding author: HAN Jian-Rong, LIU Shou-Xin,
Received Date: 31 July 2015
Available Online: 14 March 2016
Fund Project: Supported by the Ministry of Education of China (No. 208066) (No. 208066) the Education Department of Fujian Province (JA07029) (JA07029)

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 P2₁2₁2₁. 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 b-fold characteristics. Intermolecular C–H…O and N–H…O hydrogen bonds linked the molecules into a one-dimensional chain and stabilized the structure.
- tripeptide,
- N-methyl amino acid,
- synthesis,
- crystal structure,
- hydrogen bond
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