Stereochemistry of insect kinin tetrazole analogues and their diuretic activity in crickets.

• Authors: Ronald J Nachman , Geoffrey M Coast , Krzysztof Kaczmarek , Howard J Williams , Janusz Zabrocki
• Languages of publication: EN

Abstracts

EN

Insect kinin analogues of the sequence Phe-Phe-ψ[CN4]-Ala-Trp-Gly-NH2 containing (L-Phe2,L-Ala3) and (L-Phe2,D-Ala3) stereochemical variants of the tetrazole moiety, a mimic of the type VI β-turn, demonstrate significant agonist and partial antagonist activity, respectively, in a cricket diuretic bioassay. A comparison of the solution conformations of these two stereochemical variants indicates a structural basis for their divergent bioactivities. The (D-Phe2,D-Ala3) stereochemical variant was synthesized and found to demonstrate significant agonist activity. The results further define stereochemical requirements for the diuretic activity of insect kinins in crickets and provide valuable information for the design of biostable analogues capable of disrupting digestive and diuretic processes in pest insects.

Keywords

EN

constrained insect kinin analogue   tetrazole   diuresis   cis-peptide bond   β-turn mimetic  

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2004
• Volume: 51
• Issue: 1
• Pages: 121-127

Dates

published

2004

received

2003-10-31

revised

2004-01-23

accepted

2004-02-03

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