Comparison of two thioxopeptide bond photoswitches in insect kinin

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-NH_2 and H-Phe-Tyr-Ψ[CS-N]- Pro-Trp-Gly-NH_2 were studied by UV-vis absorption.The isomeri...

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Bibliographic Details
Published in:Chinese chemical letters 2010-04, Vol.21 (4), p.476-479
Main Authors: Cong, Zhi Yuan, Yang, Long Fei, Jiang, Ling, Ye, Dan, Dong, Shou Liang
Format: Article
Language:English
Subjects:
Energy barrier
Photoswitch
Thioxopeptide bond
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Summary: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-NH_2 and H-Phe-Tyr-Ψ[CS-N]- Pro-Trp-Gly-NH_2 were studied by UV-vis absorption.The isomerization energy barriers of the two segments,Ac-Phe-Ψ[CS-NH]- D-Ala-NH_2 and Ac-Tyr-Ψ[CS-N]-Pro-NH_2 picked from the two peptides,were calculated using ab initio method.The cis isomer of CS-N is more stable than...
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2009.12.033