Citation: Zhi Yuan Cong, Long Fei Yang, Ling Jiang, Dan Ye, Shou Liang Dong. Comparison of two thioxopeptide bond photoswitches in insect kinin[J]. Chinese Chemical Letters, ;2010, 21(4): 476-479. doi: 10.1016/j.cclet.2009.12.033 shu

Comparison of two thioxopeptide bond photoswitches in insect kinin

Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China

Received Date: 24 June 2009

Fund Project: This work was partially supported by the grant from National Natural Science Foundation of China (No. 30870526) and SRF for ROCS, SEM.

The photoisomerization abilities of secondary thioxopeptide bond(CS-NH)and thioxo prolyl bond(CS-N)incorporated into the C-terminal pentapeptide of insect kinin were compared.H-Phe-Phe-Ψ[CS-NH]-D-Ala-Trp-Gly-NHz and H-Phe-Tyr-Ψ[CS-N]-Pro-Trp-Gly-NH₂ were studied by UV-vis absorption.The isomerization energy barriers of the two segments,Ac-Phe-Ψ[CS-NH]-D-Ala-NH₂ and Ac-Tyr-Ψ[CS-N]-Pro-NH₂ picked from the two peptides,were calculated using ab initio method.The cis isomer of CS-N is more stable than that of CS-NH due to higher energy barrier,so the former is more suitable in peptide structure-activity relationship studies.
- Photoswitch,
- Thioxopeptide bond,
- Energy barrier
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