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Citation: SHI Zhi-Hao, WEI Yun-Yang, ZHOU Li-Ping, GU Yun-Kai. Application of N,N'-Isopropylidene Asparagine in Peptide Synthesis[J]. Chinese Journal of Applied Chemistry, ;2007, 24(6): 707-711. shu

Application of N,N'-Isopropylidene Asparagine in Peptide Synthesis

1.
Institute of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094

Corresponding author: WEI Yun-Yang,
Received Date: 3 July 2006
Available Online: 28 October 2006

A cyclic amino acid,N,N'-isopropylidene Asparagine[cAsn(acetone)],was synthesized via the reaction of L-asparagine with acetone in methanol in the presence of potassium hydroxide.Fmoc protected amino acids,Fmoc-Tyr (Bzl)-OH,Fmoc-Phe-OH,and Fmoc-Ala-OH were then allowed to react with cAsn(acetone) in DMF/CH_2>Cl₂ in the presence of 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenztriazole (HOBt) to give dipeptides Fmoc-Tyr (Bzl)-cAsn(acetone)-OH,Fmoc-Phe-cAsn(acetone)-OH and Fmoc-Ala-cAsn(acetone)-OH in yields of 35%,30% and 30% respectively.Further coupling of the dipeptide Fmoc-Tyr (Bzl)-cAsn(acetone)-OH with H-Phe-Phe-NH₂ in the presence of EDCI and HOBt led to the formation of a tetrapeptide Fmoc-Tyr (Bzl)-cAsn(acetone)-Phe-Phe-NH₂ in a yield of 70%.Deprotection of the Fmoc and Bzl groups on the tyrosine residue in the tetrapeptide with H₂/Pd-C in acetic acid gave a novel analogue of endomorphin-2(H-Tyr-cAsn(acetone)-Phe-Phe-NH₂) in a yield of 60%.¹H NMR,IR,MS and HRMS were used to characterize the structures of the titled product and the intermediates.Antinociceptive activity of the tetrapeptide was assessed in acetic acid-induced abdominal constriction tests after i.p.injected in mouse with an inhibition rate of 45% at a dose of 2.4×10^-5 g/Kg.
- N,N'-isopropylidene Asparagine,
- endomorphin,
- tetrapeptides,
- analogue
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